(1S)-3-[2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol

Details

• Internal ID: c33b5853-06e2-467e-b4b7-9317d78a237a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Vitamin D and derivatives
• IUPAC Name: (1S)-3-[2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
• SMILES (Canonical): CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
• SMILES (Isomeric): C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]2[C@@]1(CCCC2=CC=C3C[C@H](CCC3=C)O)C
• InChI: InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/t20-,23+,24-,25+,27-/m1/s1
• InChI Key: JWUBBDSIWDLEOM-DLBXBJKMSA-N
• Popularity: 4,716 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 400.60 g/mol
• Exact Mass: 400.334130642 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 6.73
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• (1S)-3-[2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
• 19356-17-3
• (1S,3Z)-3-[(2E)-2-[(3As,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
• CBiol_001814
• KBioGR_000131
• KBioSS_000131
• KBio2_000131
• KBio2_002699
• KBio2_005267
• KBio3_000261
• KBio3_000262
• Bio1_000100
• Bio1_000589
• Bio1_001078
• Bio2_000131
• Bio2_000611
• Q27166533
• (1S)-3-[2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylene-1-cyclohexanol
• (S,Z)-3-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylenecyclohexanol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9969	99.69%
Caco-2	+	0.6419	64.19%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.7857	78.57%
Subcellular localzation	Mitochondria	0.4758	47.58%
OATP2B1 inhibitior	-	0.8649	86.49%
OATP1B1 inhibitior	+	0.8185	81.85%
OATP1B3 inhibitior	+	0.8695	86.95%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8481	84.81%
P-glycoprotein inhibitior	-	0.5405	54.05%
P-glycoprotein substrate	-	0.5628	56.28%
CYP3A4 substrate	+	0.5766	57.66%
CYP2C9 substrate	-	0.7968	79.68%
CYP2D6 substrate	-	0.7741	77.41%
CYP3A4 inhibition	-	0.7968	79.68%
CYP2C9 inhibition	-	0.9229	92.29%
CYP2C19 inhibition	-	0.7885	78.85%
CYP2D6 inhibition	-	0.9488	94.88%
CYP1A2 inhibition	-	0.8874	88.74%
CYP2C8 inhibition	-	0.6221	62.21%
CYP inhibitory promiscuity	-	0.5600	56.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6374	63.74%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9698	96.98%
Skin irritation	+	0.5158	51.58%
Skin corrosion	-	0.9531	95.31%
Ames mutagenesis	-	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8449	84.49%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.9625	96.25%
skin sensitisation	+	0.5538	55.38%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.8963	89.63%
Acute Oral Toxicity (c)	I	0.5667	56.67%
Estrogen receptor binding	+	0.8900	89.00%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.7483	74.83%
Glucocorticoid receptor binding	+	0.6909	69.09%
Aromatase binding	+	0.5982	59.82%
PPAR gamma	+	0.6771	67.71%
Honey bee toxicity	-	0.8433	84.33%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9930	99.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1977	P11473	Vitamin D receptor	99.90%	99.43%
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.37%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.99%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.99%	98.95%
CHEMBL237	P41145	Kappa opioid receptor	95.98%	98.10%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.37%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	92.72%	90.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	92.60%	93.56%
CHEMBL226	P30542	Adenosine A1 receptor	92.32%	95.93%
CHEMBL233	P35372	Mu opioid receptor	89.28%	97.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.96%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.79%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.68%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.44%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.88%	100.00%
CHEMBL1902	P62942	FK506-binding protein 1A	85.83%	97.05%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.77%	92.88%
CHEMBL2996	Q05655	Protein kinase C delta	85.59%	97.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.44%	100.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	85.15%	97.47%
CHEMBL221	P23219	Cyclooxygenase-1	84.96%	90.17%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	84.34%	94.78%
CHEMBL236	P41143	Delta opioid receptor	84.25%	99.35%
CHEMBL206	P03372	Estrogen receptor alpha	83.79%	97.64%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.66%	85.31%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	82.02%	95.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.18%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.69%	93.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.59%	95.50%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.22%	98.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 166583
• LOTUS: LTS0043994
• wikiData: Q27166533