(4aR,4bR,8S,8aR,10aS)-10a-hydroxy-3,10-dimethyl-5-methylidene-8-prop-1-en-2-yl-4a,4b,6,7,8,8a-hexahydrophenanthrene-1,4-dione

Details

• Internal ID: df1da5e4-62f4-4564-88bb-57bb3e9372c1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4aR,4bR,8S,8aR,10aS)-10a-hydroxy-3,10-dimethyl-5-methylidene-8-prop-1-en-2-yl-4a,4b,6,7,8,8a-hexahydrophenanthrene-1,4-dione
• SMILES (Canonical): CC1=CC2C(CCC(=C)C2C3C1(C(=O)C=C(C3=O)C)O)C(=C)C
• SMILES (Isomeric): CC1=C[C@@H]2[C@H](CCC(=C)[C@H]2[C@@H]3[C@]1(C(=O)C=C(C3=O)C)O)C(=C)C
• InChI: InChI=1S/C20H24O3/c1-10(2)14-7-6-11(3)17-15(14)9-13(5)20(23)16(21)8-12(4)19(22)18(17)20/h8-9,14-15,17-18,23H,1,3,6-7H2,2,4-5H3/t14-,15-,17-,18+,20+/m1/s1
• InChI Key: DXRLKDVUUVHSLL-RLPRXVRJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₃
• Molecular Weight: 312.40 g/mol
• Exact Mass: 312.17254462 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.17
• H-Bond Acceptor: 3
• 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	+	0.9951	99.51%
Caco-2	-	0.5585	55.85%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6851	68.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8620	86.20%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8951	89.51%
P-glycoprotein inhibitior	-	0.8406	84.06%
P-glycoprotein substrate	-	0.7213	72.13%
CYP3A4 substrate	+	0.6096	60.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8829	88.29%
CYP3A4 inhibition	-	0.7900	79.00%
CYP2C9 inhibition	-	0.8274	82.74%
CYP2C19 inhibition	-	0.8492	84.92%
CYP2D6 inhibition	-	0.9015	90.15%
CYP1A2 inhibition	-	0.6284	62.84%
CYP2C8 inhibition	-	0.7725	77.25%
CYP inhibitory promiscuity	-	0.8689	86.89%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5237	52.37%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.9230	92.30%
Skin irritation	+	0.6185	61.85%
Skin corrosion	-	0.8945	89.45%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5912	59.12%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.6552	65.52%
skin sensitisation	+	0.5925	59.25%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6101	61.01%
Acute Oral Toxicity (c)	III	0.6715	67.15%
Estrogen receptor binding	-	0.5728	57.28%
Androgen receptor binding	+	0.6478	64.78%
Thyroid receptor binding	+	0.5395	53.95%
Glucocorticoid receptor binding	+	0.7060	70.60%
Aromatase binding	-	0.6959	69.59%
PPAR gamma	+	0.5357	53.57%
Honey bee toxicity	-	0.8912	89.12%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9745	97.45%

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	95.52%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.22%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.67%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.59%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.35%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.51%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.29%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	83.87%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.22%	89.00%
CHEMBL1871	P10275	Androgen Receptor	81.75%	96.43%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.70%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.80%	95.89%

Plants that contains it

• Jatropha curcas

Cross-Links

• PubChem: 57328375
• LOTUS: LTS0195414
• wikiData: Q104991163