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Information on EC 1.3.1.20 - trans-1,2-dihydrobenzene-1,2-diol dehydrogenase and Organism(s) Homo sapiens
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1.3.1.20 trans-1,2-dihydrobenzene-1,2-diol dehydrogenaseSpecify your search results
Word Map
- 1.3.1.20
- dihydrodiol
-
trans-dihydrodiols
- medicine
-
polycyclic
- catechols
-
nadp+-dependent
- benzenedihydrodiol
- indomethacin
-
penning
-
alpha-hydroxysteroids
- o-quinones
-
talalay
-
anti-diol
-
1.1.1.184
-
+/-trans-7,8-dihydroxy-7,8-dihydrobenzoapyrene
-
non-k-region
-
benzaanthracene
-
alicyclic
-
trans-1,2-dihydrodiols
- dicoumarol
- chrysene
-
benzoapyrene-7,8-dione
-
harvey
-
pah-induced
- androsterone
- diagnostics
The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Synonyms
trans-1,2-dihydrobenzene-1,2-diol dehydrogenase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
DDH
dehydrogenase, trans-1,2-dihydrobenzene-1,2-diol
-
-
-
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dihydrodiol dehydrogenase
additional information
-
DD4 shows only 83% sequence homology to the other human DD isoforms
DDH
member of the aldo-keto reductases superfamily which plays a central role in the metabolism of steroid hormones, prostaglandins and xenobiotics
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
isoforms belong to aldo-keto reductase superfamily
trans-1,2-dihydrobenzene-1,2-diol + NADP+ = catechol + NADPH + H+
DD4 is identical with human chlordecone reductase and 3alpha-hydroxysteroid dehydrogenase type 1, EC 1.1.1.213, catalyzes the oxidoreduction of various 3alpha-hydroxysteroids including bile acids and belong to the aldo-keto reductase superfamily, in this concern termed AKR1C4
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dehydrogenation
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-
-
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oxidation
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-
-
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redox reaction
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-
-
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reduction
reduction
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PATHWAY SOURCE
PATHWAYS
SYSTEMATIC NAME
IUBMB Comments
trans-1,2-dihydrobenzene-1,2-diol:NADP+ oxidoreductase
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CAS REGISTRY NUMBER
COMMENTARY
37255-32-6
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1-acenaphthenol + NAD(P)+
?
recombinant: DD1, DD2, and 3alpha-hydroysteroid dehydrogenase/dihydrodiol dehydrogenase
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
-
-
-
?
5beta-androstan-3,17-dione + NADPH
5beta-androstan-3alpha-ol-17-one + NADP+
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-
-
-
?
5beta-pregnan-3,20-dione + NADPH
3alpha-hydroxy-5beta-pregnan-20-one + NADP+
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-
-
-
?
trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene + NADP+
benzo[a]-pyrene-7,8-dione + NADPH
DD1, DD2, DD4, 3alpha-hydroxysteroid/dihydrodiol dehydrogenase
product is potent carcinogen
?
(S)-indan-1-ol + NADP+
?
-
DD4, wild-type and recombinant double mutant S145C/L311V
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-
?
5beta-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
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-
-
-
?
5beta-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
DD1, DD2, recombinant DD1
-
-
?
5beta-androstan-3alpha,17beta-diol + NADP+
5beta-androstan-3,17-dione + NADPH
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DD4 wild-type and mutants
-
-
?
5beta-pregnan-3,20-diol + NADP+
5beta-pregnan-20-ol-3-one + NADPH
DD1, DD2, recombinant DD1
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-
?
cholic acid + NADP+
?
-
DD4, wild-type and recombinant double mutant S145C/L311V
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-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
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-
-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
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-
-
?
trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+
catechol + NAD(P)H
DD1, DD2, recombinant DD1
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-
?
additional information
?
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involved in the metabolism of steroid hormones and polycyclic aromatic hydrocarbons, and also in the reduction of ketone-containing drugs
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-
?
additional information
?
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involved in the metabolism of steroid hormones and polycyclic aromatic hydrocarbons, and also in the reduction of ketone-containing drugs
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?
additional information
?
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enzyme-mediated oxidative damage is involved in the hydroxychavicol and benzo[a]pyrene-induced toxic effects
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-
?
additional information
?
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the enzyme is a member of the aldo-keto reductase superfamily, which normally reduces polycyclic aromatic hydrocarbons in the liver, it plays an important role in detoxification
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?
additional information
additional information
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DD4 also catalyzes oxidoreduction of 3alpha-hydroxysteroids and bile acids and is thus thought to be identical with 3alpha-hydroxysteroid dehydrogenase EC 1.1.1.213
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-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
involved in the metabolism of steroid hormones and polycyclic aromatic hydrocarbons, and also in the reduction of ketone-containing drugs
-
-
?
additional information
?
-
-
involved in the metabolism of steroid hormones and polycyclic aromatic hydrocarbons, and also in the reduction of ketone-containing drugs
-
-
?
additional information
?
-
-
enzyme-mediated oxidative damage is involved in the hydroxychavicol and benzo[a]pyrene-induced toxic effects
-
-
?
additional information
?
-
-
the enzyme is a member of the aldo-keto reductase superfamily, which normally reduces polycyclic aromatic hydrocarbons in the liver, it plays an important role in detoxification
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
chenodeoxycholic acid
DD2 very sensitive, DD1 less sensitive, recombinant DD1
chrysin
inhibits enzyme expression at concentrations higher than 0.01 mM; inhibits enzyme expression at concentrations higher than 0.01 mM
doxorubicin hydrochloride
-
50% inhibition at 0.000706 mM, parental 2008 cell, at 0.000377, 2008/C13* cell, at 0.000375 mM, 2008 cell expressing isoform 2
melphalan
-
50% inhibition at 0.009 mM, parental 2008 cell, at 0.0088, 2008/C13* cell, at 0.0057 mM, 2008 cell expressing isoform 2
paclitaxel
-
50% inhibition at 0.0000393 mM, parental 2008 cell, at 0.0000101, 2008/C13* cell, at 0.0000283 mM, 2008 cell expressing isoform 2
Ursodeoxycholic acid
very sensitiv: DD2, less sensitiv: DD1, recombinant DD1
vincristine
-
50% inhibition at 0.000021 mM, parental 2008 cell, at 0.000016, 2008/C13* cell, at 0.0000136 mM, 2008 cell expressing isoform 2
wogonin
inhibits enzyme expression at concentrations higher than 0.0025 mM; inhibits enzyme expression at concentrations higher than 0.0025 mM
carboplatin
-
50% inhibition at 0.0358 mM, parental 2008 cell, at 0.578, 2008/C13* cell, at 0.0974 mM, 2008 cell expressing isoform 1, at 0.0871 mM, 2008 cell expressing isoform 2
carboplatin
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50% inhibition at 0.036 mM, 2008 cells, at 0.578 mM, 2008/C13* cells, at 0.097 mM, cells constitutively overexpressing enzyme
cisplatin
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50% inhibition at 0.0021 mM, parental 2008 cell, at 0.0186, 2008/C13* cell, at 0.0161 mM, 2008 cell expressing isoform 1, at 0.0062 mM, 2008 cell expressing isoform 2
cisplatin
-
50% inhibition at 0.002 mM, 2008 cells, at 0.019 mM, 2008/C13* cells, at 0.016 mM, cells constitutively overexpressing enzyme
additional information
-
DD4 is inhibited by steroidal anti-inflammatory drugs
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additional information
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DD2, product inhibition and inhibition mechanism of bile acids and anti-inflammatory drugs
-
additional information
enzyme expression is not inhibited by baicalin and baicalein; enzyme expression is not inhibited by baicalin and baicalein
-
additional information
enzyme expression is not inhibited by baicalin and baicalein; enzyme expression is not inhibited by baicalin and baicalein
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.32
trans-benzene dihydrodiol
3alpha-hydroxysteroid/dihydrodiol dehydrogenase
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.015
trans-benzene dihydrodiol
3alpha-hydroxysteroid/dihydrodiol dehydrogenase
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.73
-
DD4 recombinant double mutant S145C/L311V, purified, substrate (S)-indan-1-ol
26000
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substrate 1-acenaphthol, 2008 cells constitutively overexpressing enzyme
71000
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substrate camphorquinone, 2008 cells constitutively overexpressing enzyme
additional information
additional information
-
DDH expression in resected gastric cancer specimens correlated with mortality
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
DD1, DD2, DD4, type 2 3alpha-hydroxysteroid/dihydrodiol dehydrogenase
UniProt
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
lung cancer cell line, high expression of enzyme isoform DDH1 and enzyme CYP1A1, and high level of DNA-benzo[a]pyrene adducts
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lung cancer cell line, high expression of enzyme isoform DDH1 and enzyme CYP1A1, and high level of DNA-benzo[a]pyrene adducts
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cisplatin-sensitive ovarian carcinoma cell line 2008 and its cisplatin-resistant variant 2008/C13*
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human oral epidermal carcinoma cell line OEC-M1, enzyme expression is induced by pretreatment with hydroxychavicol
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ovarian carcinoma cell A2780 and SKOV-3, cisplatin-sensitive and cisplatin-resistant cell 2008 and 2008/C13*, cervical carcinoma cell A431, germ-cell tumor Tera-2, lung adenocarcinoma cell Calu-6
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cisplatin-sensitive ovarian carcinoma cell line 2008 and its cisplatin-resistant variant 2008/C13*
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). DHDH_HUMAN
334
0
36382
Swiss-Prot
Secretory Pathway (Reliability: 4)
AK1C1_HUMAN
323
0
36788
Swiss-Prot
other Location (Reliability: 2)
AK1C2_HUMAN
323
0
36735
Swiss-Prot
other Location (Reliability: 2)
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
36000
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
L54V
-
DD1 mutant, increase in activity towards (S)-indan-1-ol and bile-acids, increased Km for trans-benzene dihydrodiol
S145C
-
native mutant with C to G replacement in DNA at position 434, no significant effect on activity
S145C/L311V
-
constructed double mutant with 3 to 5fold decreased activity for xenobiotic and steroidal substrates
additional information
additional information
-
CDD1-4 mutant consisting of DD1 with C-terminal end of DD4 shows 10-37fold increase in Km for indan-1-ol and 1,2,3,4-tetrahydronaphth-1-ol and significantly decreased activity towards androstanes, higher activity with bile-acids and 5beta-steroid than DD1
additional information
-
CDD4-1 mutant consisting of DD4 with C-terminal end of DD1shows new stereospecificity toward indan-1-ol stereomers and increased Km-values with bile acids and 3-hydroxysteroids compared to DD4
additional information
-
constitutive overexpression of enzyme in 2008 cells leads to induction of cisplatin resistance. In cisplatin-resistant cell-line 2008/C13*, differential expression of enzyme and four more genes is found
additional information
-
knock down of enzyme isoform DHH1 expression by siRNA in CL-3 cells results in 1.4- to 2.2fold increase in DNA-benzo[a]pyrene adducts
additional information
-
overexpression of enzyme in lung adenocarcinoma cell lines results in a much higher resistance to doxorubicin, cisplatin and irradiation. Isoforms DDH2 and DDH1 transfectants show higher drug and radiation resistance than DDH3 transfectants
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
DD1, DD2, DD4 and 3alpha-hydroxysteroid dehydrogenase/dehydrodiol dehydrogenase, all recombinant from Escherichia coli
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
DD1, DD2, DD4, type 2 3alpha-hydroxysteroid/dihydrodiol dehydrogenase, expression in Escherichia coli
DD4, isolation of mRNA of native mutants isolated from a liver sample, synthesis of cDNA by RT-PCR, polymorphism of DD4 gene
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
diagnostics
-
overexpression of dihydrodiol dehydrogenase as a prognostic marker in resected gastric cancer patients, patients with DDH overexpression have a significantly higher incidence of early tumor recurrence and distant metastasis
medicine
medicine
-
enzyme overexpression is detected in 66.9% of pathological sections and in 41.6% of metastatic lymph nodes in patients with esophageal squamous cell carcinoma, the major isoform is DDH2. Enzyme overexpression is positively correlated with smoking habit, tumor stage, number of metastatic lymph nodes, lymphovascular invasion and COX-2 expression, and inversely correlated with glutathione-S-transferase and nm23-HI expression. Patients with low enzyme expression have significantly lower incidence of tumor recurrences and better survival
medicine
-
expression of enzyme isoforms 1 and 2 is detected in 59.6% of pathologicla sections, enzyme expression is significantly higher in patients with tumor size over 2 cm, an in those who had early local recurrence. enzyme expression correlates with those of COX-2, interleukin-6, microsomal epoxide hydrolase and soluble epoxide hydrolase in patients. It is inversely correlated with expression of glutathione S-transferase and NADPH p450 reductase
medicine
-
enzyme is expressed in a high percentage of primary ovarian tumors and may be associated with cisplatin-based chemotherapy resistance
medicine
-
high expression level of enzyme in A431 squamous cell carcinoma, which is barely detectable in other normal or malignant cutaneous cells, including keratinocytes
medicine
-
reduction of enzyme expression in lung tumors may contribute to an increase in DNA adduct levels and may partly be responsible for the higher susceptibility of female lung cancer patients to DNA damage. Detection of DNA adducts correlates with CYP1A1-positive tumors, but not with isoform DDH1-positive tumors
medicine
-
resistance to doxorubicin and cisplatin in lung adenocarcinoma cell lines is closely associated with enzyme isoforms DDH1 and DDH2 activity
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Aoki, S.; Ishikura, S.; Asada, Y.; Usami, N.; Hara, A.
Identity of dimeric dihydrodiol dehydrogenase as NADP+-dependent D-xylose dehydrogenase in pig liver
Chem. Biol. Interact.
130-132
775-784
2001
Canis sp., Homo sapiens, Macaca fuscata, Oryctolagus cuniculus, Sus scrofa
Kume, T.; Iwasa, H.; Shiraishi, H.; Yokoi, T.; Nagashima, K.; Otsuka, M.; Terada, T.; Takagi, T.; Hara, A.; Kamataki, T.
Characterization of a novel variant (S145C/L311V) of 3alpha-hydroxysteroid/dihydrodiol dehydrogenase in human liver
Pharmacogenetics
9
763-771
1999
Homo sapiens
Miyabe, Y.; Amano, T.; Deyashiki, Y.; Hara, A.; Tsukada, F.
Kinetic studies of the inhibition of a human liver 3alpha-hydroxysteroid/dihydrodiol dehydrogenase isozyme by bile acids and anti-inflammatory drugs
Biol. Pharm. Bull.
18
9-12
1995
Homo sapiens
Deyashiki, Y.; Tamada, Y.; Miyabe, Y.; Nakanishi, M.; Matsuura, K.; Hara, A.
Expression and kinetic properties of a recombinant 3alpha-hydroxysteroid/dihydrodiol dehydrogenase isoenzyme of human liver
J. Biochem.
118
285-290
1995
Homo sapiens
Hara, A.; Matsuura, K.; Tamada, Y.; Sato, K.; Miyabe, Y.; Deyashiki, Y.; Ishida, N.
Relationship of human liver dihydrodiol dehydrogenases to hepatic bile-acid-binding protein and an oxidoreductase of human colon cells
Biochem. J.
313
373-376
1996
Homo sapiens (Q04828)
Burczynski, M.E.; Harvey, R.G.; Penning, T.M.
Expression and characterization of four recombinant human dihydrodiol dehydrogenase isoforms: oxidation of trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene to the activated o-quinone metabolite benzo[a]pyrene-7,8-dione
Biochemistry
37
6781-6790
1998
Homo sapiens (P42330)
Matsuura, K.; Hara, A.; Deyashiki, Y.; Iwasa, H.; Kume, T.; Ishikura, S.; Shiraishi, H.; Katagiri, Y.
Roles of the C-terminal domains of human dihydrodiol dehydrogenase isoforms in the binding of substrates and modulators: probing with chimeric enzymes
Biochem. J.
336
429-436
1998
Homo sapiens
Matsuura, K.; Deyashiki, Y.; Sato, K.; Ishida, N.; Miwa, G.; Hara, A.
Identification of amino acid residues responsible for differences in substrate specificity and inhibitor sensitivity between two human liver dihydrodiol dehydrogenase isoenzymes by site-directed mutagenesis
Biochem. J.
323
61-64
1997
Homo sapiens
Deng, H.B.; Adikari, M.; Parekh, H.K.; Simpkins, H.
Ubiquitous induction of resistance to platinum drugs in human ovarian, cervical, germ-cell and lung carcinoma tumor cells overexpressing isoforms 1 and 2 of dihydrodiol dehydrogenase
Cancer Chemother. Pharmacol.
54
301-307
2004
Homo sapiens
Wang, L.S.; Chow, K.C.; Wu, Y.C.; Lin, T.Y.; Li, W.Y.
Inverse expression of dihydrodiol dehydrogenase and glutathione-S-transferase in patients with esophageal squamous cell carcinoma
Int. J. Cancer
111
246-251
2004
Homo sapiens
Deng, H.B.; Parekh, H.K.; Chow, K.C.; Simpkins, H.
Increased expression of dihydrodiol dehydrogenase induces resistance to cisplatin in human ovarian carcinoma cells
J. Biol. Chem.
277
15035-15043
2002
Homo sapiens
Yang, M.D.; Wu, C.C.; Chiou, S.H.; Chiu, C.F.; Lin, T.Y.; Chiang, I.P.; Chow, K.C.
Reduction of dihydrodiol dehydrogenase expression in resected hepatocellular carcinoma
Oncol. Rep.
10
271-276
2003
Homo sapiens
Tang, D.W.; Chang, K.W.; Chi, C.W.; Liu, T.Y.
Hydroxychavicol modulates benzo[a]pyrene-induced genotoxicity through induction of dihydrodiol dehydrogenase
Toxicol. Lett.
152
235-243
2004
Homo sapiens
Hung, J.J.; Chow, K.C.; Wang, H.W.; Wang, L.S.
Expression of dihydrodiol dehydrogenase and resistance to chemotherapy and radiotherapy in adenocarcinoma cells of lung
Anticancer Res.
26
2949-2956
2006
Homo sapiens
Cheng, Y.W.; Tsai, H.J.; Wu, J.Y.; Hsu, Y.F.; Chen, C.Y.; Hao, N.J.; Lee, H.
A possible role for dihydrodiol dehydrogenase in the formation of benzo[a]pyrene-DNA adducts in lung cancer cells and tumor tissues
Environ. Mol. Mutagen.
48
14-21
2006
Homo sapiens
Chen, Y.J.; Yuan, C.C.; Chow, K.C.; Wang, P.H.; Lai, C.R.; Yen, M.S.; Wang, L.S.
Overexpression of dihydrodiol dehydrogenase is associated with cisplatin-based chemotherapy resistance in ovarian cancer patients
Gynecol. Oncol.
97
110-117
2005
Homo sapiens
Chow, K.C.; Lu, M.P.; Wu, M.T.
Expression of dihydrodiol dehydrogenase plays important roles in apoptosis- and drug-resistance of A431 squamous cell carcinoma
J. Dermatol. Sci.
41
205-212
2006
Homo sapiens
Pan, B.F.; Nelson, J.A.
Dihydrodiol dehydrogenase in drug resistance and sensitivity of human carcinomas
Cancer Chemother. Pharmacol.
59
697-702
2007
Homo sapiens
Wang, H.W.; Lin, C.P.; Chiu, J.H.; Chow, K.C.; Kuo, K.T.; Lin, C.S.; Wang, L.S.
Reversal of inflammation-associated dihydrodiol dehydrogenases (AKR1C1 and AKR1C2) overexpression and drug resistance in nonsmall cell lung cancer cells by wogonin and chrysin
Int. J. Cancer
120
2019-2027
2007
Homo sapiens (P52895), Homo sapiens (Q04828)
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