Hydroxyprogesterone

Details

• Internal ID: b51f1946-194a-4a2a-b9bb-53aac4cb2d42
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Pregnane steroids > Gluco/mineralocorticoids, progestogins and derivatives
• IUPAC Name: (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• SMILES (Canonical): CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O
• SMILES (Isomeric): CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O
• InChI: InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1
• InChI Key: DBPWSSGDRRHUNT-CEGNMAFCSA-N
• Popularity: 4,338 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.50 g/mol
• Exact Mass: 330.21949481 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.84
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 17ALPHA-HYDROXYPROGESTERONE
• 68-96-2
• 17-Hydroxyprogesterone
• 17a-Hydroxyprogesterone
• Prodix
• Prodox
• Gestageno gador
• Pregn-4-ene-3,20-dione, 17-hydroxy-
• Setaderm
• Oxiprogesteronum
• 17-alpha-Hydroxyprogesterone
• 17-Hydroxypregn-4-ene-3,20-dione
• 17alpha-Hydroxy-4-pregnene-3,20-dione
• 17alpha-Hydroxy-progesterone
• Hidroxiprogesterona
• Hydroxyprogesteronum
• Pregn-4-ene-3,20-dione-17-ol
• Gestageno
• Idrossiprogesterone [DCIT]
• delta(4)-Pregnene-17alpha-ol-3,20-dione
• 17|A-Hydroxyprogesterone
• Hydroxyprogesteronum [INN-Latin]
• Hidroxiprogesterona [INN-Spanish]
• 17-OH Progesterone
• 17-Hydroxypregn-4-en-3,20-dione
• 17.alpha.-Hydroxyprogesterone
• 604-09-1
• HSDB 3343
• alpha Hydroxy progesterone
• Idrossiprogesterone
• 17OHP
• Hydroxyprogesterone [INN:BAN]
• CHEBI:17252
• EINECS 200-699-4
• NSC 15468
• NSC-15468
• 17alpha hydroxyprogesterone
• BRN 2062088
• MLS000028453
• MLS001076300
• 17-OHP
• (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• DTXSID6040747
• 4-Pregnen-17a-ol-3,20-dione
• U 3096
• UNII-21807M87J2
• Pregn-4-ene-3,20-dione, 17-hydroxy-, (17a)-
• 4-Pregnen-17alpha-ol-3,20-dione
• Delta4-Pregnen-17alpha-ol-3,20-dione
• NCGC00093949-03
• alpha-17Hydroxypregn-4-ene-3,20-dione
• SMR000058349
• 21807M87J2
• Hydroxyprogesterone (INN)
• (9beta)-17-Hydroxypregn-4-Ene-3,20-Dione
• U-3096
• 4-08-00-02189 (Beilstein Handbook Reference)
• DTXCID4020747
• Pregn-4-ene-3,20-dione, 17-hydroxy-, (17.alpha.)-
• HYDROXYPROGESTERONE [INN]
• CAS-68-96-2
• MFCD00003659
• hydroxyprogesteron-
• 3QZ
• 17-Hydroxyprogeoterone
• 17-hydroxy-progesterone
• 17-a-Hydroxyprogesterone
• 17.alpha.-Pregn-4-ene-3,20-dione, 17-hydroxy-
• Opera_ID_1812
• 17?-Hydroxy Progesterone
• bmse000472
• bmse000598
• D06WBH
• Epitope ID:152220
• SCHEMBL8068
• CHEMBL1062
• BIDD:PXR0103
• Lopac0_000565
• 17.alpha.-Hydoxyprogesterone
• MLS002695950
• GTPL5104
• Progesterone, 17alpha-hydroxy-
• Pregn-4-ene-3, 17-hydroxy-
• DTXSID00859075
• HYDROXYPROGESTERONE [HSDB]
• HMS2090M08
• HMS2234J04
• HMS3261B12
• HYDROXYPROGESTERONE [VANDF]
• D4-Pregnen-17a-ol-3,20-dione
• HY-B0891
• NSC15468
• Pregn-4-en-17a-ol-3,20-dione
• HYDROXYPROGESTERONE [WHO-DD]
• Tox21_111233
• Tox21_301530
• Tox21_500565
• BDBM50423511
• LMST02030161
• s4507
• 17alpha-Hydroxyprogesterone, >=95%
• 17a-Hydroxypregn-4-ene-3,20-dione
• AKOS015955623
• Tox21_111233_1
• CCG-204655
• CS-4354
• CS-O-10309
• DB14570
• FD12004
• KS-5312
• LP00565
• SDCCGSBI-0050548.P002
• 4-Pregnen-17.alpha.-ol-3,20-dione
• NCGC00093949-04
• NCGC00093949-05
• NCGC00093949-08
• NCGC00255425-01
• NCGC00261250-01
• 17alpha-hydroxy-pregn-4-ene-3,20-dione
• 17.ALPHA.-HYDROXYPROGESTERONE [MI]
• LS-118696
• 17.alpha.-Hydroxypregna-4-ene-3,20-dione
• EU-0100565
• H1250
• C01176
• D08052
• H 5752
• 17-Hydroxypregn-4-ene-3,20-dione, (+/-)-
• AB00490003-08
• Q175901
• 17.ALPHA.-HYDROXYPREGN-4-ENE-3,20-DIONE
• W-104646
• 17-Hydroxypregn-4-ene-3,20-dione-, (17.alpha.)-
• 7A45BEF6-ADD0-4B3E-A014-2DE930D3B67B
• 17alpha-Hydroxyprogesterone, VETRANAL(TM), analytical standard
• (1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
• (8R,10R,13S,17R)-17-Acetyl-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
• (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
• 110850-01-6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8857	88.57%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8483	84.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9727	97.27%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.9500	95.00%
BSEP inhibitior	+	0.9333	93.33%
P-glycoprotein inhibitior	+	0.8915	89.15%
P-glycoprotein substrate	-	0.6806	68.06%
CYP3A4 substrate	+	0.7519	75.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8953	89.53%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.6103	61.03%
CYP2D6 inhibition	-	0.9506	95.06%
CYP1A2 inhibition	-	0.9425	94.25%
CYP2C8 inhibition	+	0.5463	54.63%
CYP inhibitory promiscuity	-	0.9304	93.04%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5040	50.40%
Eye corrosion	-	0.9945	99.45%
Eye irritation	-	0.9808	98.08%
Skin irritation	+	0.7349	73.49%
Skin corrosion	-	0.9429	94.29%
Ames mutagenesis	-	0.8679	86.79%
Human Ether-a-go-go-Related Gene inhibition	-	0.3827	38.27%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.7124	71.24%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	IV	0.5200	52.00%
Estrogen receptor binding	+	0.9007	90.07%
Androgen receptor binding	+	0.9139	91.39%
Thyroid receptor binding	+	0.8355	83.55%
Glucocorticoid receptor binding	+	0.9100	91.00%
Aromatase binding	+	0.8021	80.21%
PPAR gamma	-	0.6799	67.99%
Honey bee toxicity	-	0.8102	81.02%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9900	99.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL256	P0DMS8	Adenosine A3 receptor	4730 nM	IC50	via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	5011.9 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2421	P08185	Corticosteroid binding globulin	18.2 nM	Ki	PMID: 15139751
CHEMBL238	Q01959	Dopamine transporter	6905 nM	IC50	via CMAUP
CHEMBL2034	P04150	Glucocorticoid receptor	51 nM	IC50	via CMAUP
CHEMBL3385	P27361	MAP kinase ERK1	3157 nM	IC50	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	25118.9 nM; 5623.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	2238.7 nM	Potency	via CMAUP
CHEMBL3305	P04278	Testis-specific androgen-binding protein	100 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1994	P08235	Mineralocorticoid receptor	96.74%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.76%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.59%	91.11%
CHEMBL1871	P10275	Androgen Receptor	93.17%	96.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.22%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.98%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	86.30%	91.19%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	86.19%	94.78%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.98%	97.25%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	85.26%	85.30%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.44%	82.69%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.41%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.36%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.23%	85.14%

Plants that contains it

• Linum usitatissimum
• Vitex agnus-castus

Cross-Links

• PubChem: 6238
• NPASS: NPC144258
• ChEMBL: CHEMBL1062
• LOTUS: LTS0226374
• wikiData: Q175901