(4aR,4bR,5S,7S,8aR,10aS)-7-ethenyl-5-hydroxy-4b,7,10a-trimethyl-1-methylidene-5,6,8,8a,9,10-hexahydro-4aH-phenanthren-4-one

Details

• Internal ID: 61b14d34-547d-40a9-8bd9-21ff4f1213da
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4aR,4bR,5S,7S,8aR,10aS)-7-ethenyl-5-hydroxy-4b,7,10a-trimethyl-1-methylidene-5,6,8,8a,9,10-hexahydro-4aH-phenanthren-4-one
• SMILES (Canonical): CC12CCC3CC(CC(C3(C1C(=O)C=CC2=C)C)O)(C)C=C
• SMILES (Isomeric): C[C@]12CC[C@@H]3C[C@](C[C@@H]([C@]3([C@@H]1C(=O)C=CC2=C)C)O)(C)C=C
• InChI: InChI=1S/C20H28O2/c1-6-18(3)11-14-9-10-19(4)13(2)7-8-15(21)17(19)20(14,5)16(22)12-18/h6-8,14,16-17,22H,1-2,9-12H2,3-5H3/t14-,16+,17-,18+,19-,20+/m1/s1
• InChI Key: PCYIYFKJVBYGAH-UFGPKIGGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.40 g/mol
• Exact Mass: 300.208930132 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.07
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9974	99.74%
Caco-2	+	0.7913	79.13%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5665	56.65%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.9063	90.63%
OATP1B3 inhibitior	+	0.9356	93.56%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6750	67.50%
BSEP inhibitior	-	0.8459	84.59%
P-glycoprotein inhibitior	-	0.8850	88.50%
P-glycoprotein substrate	-	0.8513	85.13%
CYP3A4 substrate	+	0.6158	61.58%
CYP2C9 substrate	-	0.8117	81.17%
CYP2D6 substrate	-	0.8662	86.62%
CYP3A4 inhibition	-	0.6632	66.32%
CYP2C9 inhibition	-	0.8574	85.74%
CYP2C19 inhibition	-	0.6960	69.60%
CYP2D6 inhibition	-	0.9488	94.88%
CYP1A2 inhibition	-	0.7470	74.70%
CYP2C8 inhibition	-	0.7990	79.90%
CYP inhibitory promiscuity	-	0.9043	90.43%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5483	54.83%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8732	87.32%
Skin irritation	+	0.6833	68.33%
Skin corrosion	-	0.9643	96.43%
Ames mutagenesis	-	0.8664	86.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7393	73.93%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	+	0.5283	52.83%
skin sensitisation	+	0.5570	55.70%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4764	47.64%
Acute Oral Toxicity (c)	III	0.8982	89.82%
Estrogen receptor binding	+	0.6615	66.15%
Androgen receptor binding	+	0.5598	55.98%
Thyroid receptor binding	+	0.6782	67.82%
Glucocorticoid receptor binding	+	0.5756	57.56%
Aromatase binding	+	0.6470	64.70%
PPAR gamma	-	0.6392	63.92%
Honey bee toxicity	-	0.8507	85.07%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9893	98.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.04%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.42%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.65%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	89.57%	91.49%
CHEMBL2581	P07339	Cathepsin D	89.21%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.09%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.82%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	85.55%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.34%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.53%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.29%	97.25%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.82%	93.03%

Plants that contains it

• Simira eliezeriana

Cross-Links

• PubChem: 163076027
• LOTUS: LTS0152435
• wikiData: Q105206172