(3S,8S,9S,10R,11R,13S,14S,16S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,11,16-triol

Details

• Internal ID: b8efd0ec-aed9-4795-bb6d-c5013d464b5f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Ergostane steroids > Ergosterols and derivatives
• IUPAC Name: (3S,8S,9S,10R,11R,13S,14S,16S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,11,16-triol
• SMILES (Canonical): CC(C)C(=C)CCC(C)C1C(CC2C1(CC(C3C2CC=C4C3(CCC(C4)O)C)O)C)O
• SMILES (Isomeric): C[C@H](CCC(=C)C(C)C)[C@H]1[C@H](C[C@@H]2[C@@]1(C[C@H]([C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)O)C)O
• InChI: InChI=1S/C28H46O3/c1-16(2)17(3)7-8-18(4)25-23(30)14-22-21-10-9-19-13-20(29)11-12-27(19,5)26(21)24(31)15-28(22,25)6/h9,16,18,20-26,29-31H,3,7-8,10-15H2,1-2,4-6H3/t18-,20+,21+,22+,23+,24-,25+,26-,27+,28+/m1/s1
• InChI Key: OAICOSKBQLOMBW-SOHCERLJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₆O₃
• Molecular Weight: 430.70 g/mol
• Exact Mass: 430.34469533 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.50
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9967	99.67%
Caco-2	-	0.5623	56.23%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6093	60.93%
OATP2B1 inhibitior	-	0.7224	72.24%
OATP1B1 inhibitior	+	0.8974	89.74%
OATP1B3 inhibitior	+	0.9283	92.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6759	67.59%
P-glycoprotein inhibitior	-	0.6090	60.90%
P-glycoprotein substrate	+	0.6601	66.01%
CYP3A4 substrate	+	0.6977	69.77%
CYP2C9 substrate	-	0.6499	64.99%
CYP2D6 substrate	-	0.6843	68.43%
CYP3A4 inhibition	-	0.7995	79.95%
CYP2C9 inhibition	-	0.9147	91.47%
CYP2C19 inhibition	-	0.8526	85.26%
CYP2D6 inhibition	-	0.9470	94.70%
CYP1A2 inhibition	-	0.9384	93.84%
CYP2C8 inhibition	+	0.6358	63.58%
CYP inhibitory promiscuity	-	0.6169	61.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6493	64.93%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.9643	96.43%
Skin irritation	+	0.5415	54.15%
Skin corrosion	-	0.9482	94.82%
Ames mutagenesis	-	0.8578	85.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7326	73.26%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.5658	56.58%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.6546	65.46%
Acute Oral Toxicity (c)	I	0.5110	51.10%
Estrogen receptor binding	+	0.7675	76.75%
Androgen receptor binding	+	0.7375	73.75%
Thyroid receptor binding	+	0.6800	68.00%
Glucocorticoid receptor binding	+	0.7578	75.78%
Aromatase binding	+	0.5557	55.57%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.6479	64.79%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9957	99.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.92%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.23%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.08%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.93%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	93.78%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	92.58%	97.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.54%	100.00%
CHEMBL2581	P07339	Cathepsin D	92.34%	98.95%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	91.05%	89.05%
CHEMBL226	P30542	Adenosine A1 receptor	90.46%	95.93%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.45%	82.69%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.92%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.75%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.97%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.86%	96.61%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.84%	93.56%
CHEMBL237	P41145	Kappa opioid receptor	83.15%	98.10%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.80%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.31%	92.62%
CHEMBL1871	P10275	Androgen Receptor	81.20%	96.43%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.87%	100.00%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	80.05%	95.34%

Plants that contains it

• Hippophae rhamnoides

Cross-Links

• PubChem: 102078084
• NPASS: NPC19607