5alpha-Dihydroprogesterone

Details

• Internal ID: 1dedc653-4b9b-4ad4-be2f-43b5158a23d9
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Pregnane steroids > Gluco/mineralocorticoids, progestogins and derivatives
• IUPAC Name: (5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• InChI: InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1
• InChI Key: XMRPGKVKISIQBV-BJMCWZGWSA-N
• Popularity: 513 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₂
• Molecular Weight: 316.50 g/mol
• Exact Mass: 316.240230259 g/mol
• Topological Polar Surface Area (TPSA): 34.10 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.80
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 5alpha-Pregnane-3,20-dione
• 3,20-Allopregnanedione
• 5-alpha-Dihydroprogesterone
• 5alpha-Dihydroprogesterone
• 3,20-Dioxo-5alpha-pregnane
• 98G4S1OH0Z
• (5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• DTXSID301017277
• NSC-18319
• CHEBI:28952
• 5alpha DHP
• 5alpha-DHP
• 5beta DHP
• 5beta-DHP
• 5 alpha Pregnanedione
• 5-alpha-Pregnanedione
• 3,20 Allopregnanedione
• 5 beta Dihydroprogesterone
• 5 alpha Dihydroprogesterone
• 5 alpha-Dihydroprogesterone
• 5alpha Pregnane 3,20 dione
• 5 beta Pregnane 3,20 dione
• 5 beta-Pregnane-3,20-dione
• 5 alpha Pregnane 3,20 dione
• 5 alpha-Pregnane-3,20-dione
• (5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta(a)phenanthren-3-one
• RefChem:531917
• DTXCID601475484
• 3,20-Allopregnanedione, (5alpha)-
• 209-297-3
• 5a-Pregnane-3,20-dione
• allopregnandione
• Allopregnan-3,20-dione
• 5alpha-Pregnan-3,20-dione
• 5.alpha.-Dihydroprogesterone
• MFCD00067132
• NSC 18319
• (5alpha)-pregnane-3,20-dione
• 3,20-Dioxo-5.alpha.-pregnane
• 5.alpha.-Pregnane-3,20-dione
• (5a)-Pregnane-3,20-dione
• CHEMBL407717
• 5alpha-Pregnane-3,20-dione (allo)
• Pregnane-3,20-dione, (5.alpha.)-
• 5.beta.-Pregnane-3,20-dione
• 5b-pregnane-3,20-dione
• Pregnane-3,20-dione, (5a)-
• Pregnane-3,20-dione, (5alpha)-
• EINECS 209-297-3
• Allopregnane-3,20-dione
• 5.alpha.-Pregnan-3,20-dione
• BRN 2058506
• UNII-98G4S1OH0Z
• 5|A-pregnane-3,20-dione
• (5.alpha.)-Pregnane-3,20-dione
• 5A-pregnane-3-20-dione-allo
• allo-pregnandione
• Allodihydroprogeserone
• 5a-Dihydroprogesterone
• 5a-Pregnan-3,20-dione
• bmse000490
• 3,20-Dioxo-5a-pregnane
• 5 a-pregnane-3 20-dione
• 5 a-pregnane-3,20-dione
• BIDD:PXR0089
• SCHEMBL37778
• 4-07-00-02199 (Beilstein Handbook Reference)
• 5alpha-Pregnane 3,20-dione
• Pregnane-3, (5.alpha.)-
• 5alpha-pregnan-3,20 -dione
• orb1301696
• MSK8588
• 5alpha-pregnane-3,20-dione(allo)
• NSC18319
• BDBM50375561
• LMST02030170
• MSK8588-100A
• s3206
• Pregnane-3,20-dione, 5alpha-allo-
• 3,20-ALLOPREGNANEDIONE [MI]
• AKOS015895181
• MSK8588-1000A
• CS-W006492
• EBC-615994
• FP40764
• HY-W006492
• (1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-acetyl-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-7-one
• AS-15992
• PD099522
• SY076242
• P2423
• WLN: L E5 B666 OVTJ A1 E1 FV1
• 5f inverted question mark-Pregnane-3,20-dione
• C03681
• Q28487660
• 5alpha-Pregnane-3,20-dione (allo), progesterone metabolite
• 4C28DCDC-9872-4488-85F5-6D25C01E9A45
• (5alpha)-Pregnane-3,20-dione Solution in Acetonitrile, 1000ug/mL
• (5alpha)-Pregnane-3,20-dione Solution in Acetonitrile, 100ug/mL
• (5S,8R,9S,10S,13S,14S,17S)-17-Acetyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one
• (5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.7148	71.48%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6639	66.39%
OATP2B1 inhibitior	-	0.8768	87.68%
OATP1B1 inhibitior	-	0.3473	34.73%
OATP1B3 inhibitior	+	0.9852	98.52%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.7500	75.00%
BSEP inhibitior	+	0.8077	80.77%
P-glycoprotein inhibitior	+	0.8608	86.08%
P-glycoprotein substrate	-	0.7937	79.37%
CYP3A4 substrate	+	0.7385	73.85%
CYP2C9 substrate	-	0.7813	78.13%
CYP2D6 substrate	-	0.7531	75.31%
CYP3A4 inhibition	-	0.8767	87.67%
CYP2C9 inhibition	-	0.8701	87.01%
CYP2C19 inhibition	-	0.8818	88.18%
CYP2D6 inhibition	-	0.9691	96.91%
CYP1A2 inhibition	-	0.8660	86.60%
CYP2C8 inhibition	-	0.8740	87.40%
CYP inhibitory promiscuity	-	0.9574	95.74%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5671	56.71%
Eye corrosion	-	0.9724	97.24%
Eye irritation	-	0.8856	88.56%
Skin irritation	+	0.6403	64.03%
Skin corrosion	-	0.8813	88.13%
Ames mutagenesis	-	0.7960	79.60%
Human Ether-a-go-go-Related Gene inhibition	-	0.5964	59.64%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	+	0.7622	76.22%
skin sensitisation	+	0.6383	63.83%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7971	79.71%
Acute Oral Toxicity (c)	III	0.7431	74.31%
Estrogen receptor binding	+	0.8685	86.85%
Androgen receptor binding	+	0.8025	80.25%
Thyroid receptor binding	+	0.6769	67.69%
Glucocorticoid receptor binding	+	0.9017	90.17%
Aromatase binding	+	0.6454	64.54%
PPAR gamma	-	0.6305	63.05%
Honey bee toxicity	-	0.8557	85.57%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9648	96.48%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	290 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.53%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.67%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.10%	91.11%
CHEMBL1871	P10275	Androgen Receptor	86.94%	96.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.73%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.77%	98.95%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.23%	93.04%
CHEMBL1902	P62942	FK506-binding protein 1A	82.97%	97.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.91%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.52%	96.38%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.36%	93.03%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.35%	85.30%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.70%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	80.65%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.00%	99.23%

Plants that contains it

• Holarrhena pubescens

Cross-Links

• PubChem: 92810
• LOTUS: LTS0186631
• wikiData: Q4641508