7-Oxostigmasterol

Details

• Internal ID: 94c9f73f-f95a-48c9-8f79-3d3dc864ac76
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Stigmastanes and derivatives
• IUPAC Name: (3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-3-hydroxy-10,13-dimethyl-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
• SMILES (Canonical): CCC(C=CC(C)C1CCC2C1(CCC3C2C(=O)C=C4C3(CCC(C4)O)C)C)C(C)C
• SMILES (Isomeric): CC[C@H](/C=C/[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C(=O)C=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C
• InChI: InChI=1S/C29H46O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-27-25(13-15-29(23,24)6)28(5)14-12-22(30)16-21(28)17-26(27)31/h8-9,17-20,22-25,27,30H,7,10-16H2,1-6H3/b9-8+/t19-,20-,22+,23-,24+,25+,27+,28+,29-/m1/s1
• InChI Key: UKMCCFHULJHJNS-RVFLFKIDSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₆O₂
• Molecular Weight: 426.70 g/mol
• Exact Mass: 426.349780706 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 7.50
• Atomic LogP (AlogP): 6.98
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• CHEMBL2376389
• SCHEMBL13833044
• CHEBI:191553
• DTXSID401316179
• Stigmasta-5,22-dien-3.beta.-ol-3-one
• (3S,8S,9S,10R,13R,14S,17R)-17-[(E,1R,4S)-4-ethyl-1,5-dimethyl-hex-2-enyl]-3-hydroxy-10,13-dimethyl-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
• (3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-3-hydroxy-10,13-dimethyl-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
• 36449-99-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5052	50.52%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6509	65.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8470	84.70%
OATP1B3 inhibitior	+	0.9887	98.87%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.7631	76.31%
P-glycoprotein inhibitior	+	0.7067	70.67%
P-glycoprotein substrate	+	0.5657	56.57%
CYP3A4 substrate	+	0.6986	69.86%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.8843	88.43%
CYP3A4 inhibition	-	0.8167	81.67%
CYP2C9 inhibition	-	0.9299	92.99%
CYP2C19 inhibition	-	0.8821	88.21%
CYP2D6 inhibition	-	0.9408	94.08%
CYP1A2 inhibition	-	0.9484	94.84%
CYP2C8 inhibition	-	0.6699	66.99%
CYP inhibitory promiscuity	-	0.6720	67.20%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5525	55.25%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9594	95.94%
Skin irritation	+	0.5508	55.08%
Skin corrosion	-	0.9676	96.76%
Ames mutagenesis	-	0.7678	76.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.5334	53.34%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	+	0.5224	52.24%
skin sensitisation	+	0.5678	56.78%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8248	82.48%
Acute Oral Toxicity (c)	III	0.5069	50.69%
Estrogen receptor binding	+	0.8458	84.58%
Androgen receptor binding	+	0.8435	84.35%
Thyroid receptor binding	+	0.5997	59.97%
Glucocorticoid receptor binding	+	0.7706	77.06%
Aromatase binding	-	0.5889	58.89%
PPAR gamma	+	0.5461	54.61%
Honey bee toxicity	-	0.8083	80.83%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9923	99.23%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	98.11%	95.93%
CHEMBL2581	P07339	Cathepsin D	97.44%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.27%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.80%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.59%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	92.49%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.68%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.64%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.78%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.56%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.46%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	84.85%	90.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.88%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.06%	89.00%
CHEMBL1871	P10275	Androgen Receptor	81.55%	96.43%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.45%	93.04%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.42%	86.33%
CHEMBL255	P29275	Adenosine A2b receptor	81.22%	98.59%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.57%	95.71%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.18%	82.69%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.16%	85.30%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.06%	100.00%

Plants that contains it

• Acorus calamus
• Brassica rapa
• Costus tonkinensis
• Euphorbia fischeriana
• Gynura japonica
• Iris missouriensis
• Joannesia princeps
• Knoxia roxburghii
• Leucas cephalotes
• Ornithopus sativus
• Oryza sativa
• Phaseolus vulgaris
• Solanum violaceum
• Sphagneticola trilobata

Cross-Links

• PubChem: 12044013
• NPASS: NPC58063
• LOTUS: LTS0025704
• wikiData: Q104375113