(3aR,6aS,7R,10aS,10bR)-3a-hydroxy-2,5-dimethyl-10-methylidene-7-prop-1-en-2-yl-6a,7,8,9,10a,10b-hexahydrobenzo[h]azulene-1,4-dione

Details

• Internal ID: f837001c-ccd5-4d38-bc21-ceece4e931c9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Rhamnofolane and daphnane diterpenoids
• IUPAC Name: (3aR,6aS,7R,10aS,10bR)-3a-hydroxy-2,5-dimethyl-10-methylidene-7-prop-1-en-2-yl-6a,7,8,9,10a,10b-hexahydrobenzo[h]azulene-1,4-dione
• SMILES (Canonical): CC1=CC2C(CCC(=C)C2C3C(=O)C(=CC3(C1=O)O)C)C(=C)C
• SMILES (Isomeric): CC1=C[C@H]2[C@@H](CCC(=C)[C@@H]2[C@H]3C(=O)C(=C[C@@]3(C1=O)O)C)C(=C)C
• InChI: InChI=1S/C20H24O3/c1-10(2)14-7-6-11(3)16-15(14)8-12(4)19(22)20(23)9-13(5)18(21)17(16)20/h8-9,14-17,23H,1,3,6-7H2,2,4-5H3/t14-,15-,16-,17-,20+/m0/s1
• InChI Key: GLIADXUPICDEPH-DRCYAFTPSA-N
• Popularity: 0 references 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: 3.00
• 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	+	0.9935	99.35%
Caco-2	+	0.5608	56.08%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5947	59.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9117	91.17%
OATP1B3 inhibitior	+	0.9402	94.02%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.8480	84.80%
P-glycoprotein inhibitior	-	0.8093	80.93%
P-glycoprotein substrate	-	0.7059	70.59%
CYP3A4 substrate	+	0.5710	57.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8829	88.29%
CYP3A4 inhibition	-	0.8675	86.75%
CYP2C9 inhibition	-	0.8414	84.14%
CYP2C19 inhibition	-	0.8618	86.18%
CYP2D6 inhibition	-	0.9140	91.40%
CYP1A2 inhibition	-	0.6250	62.50%
CYP2C8 inhibition	-	0.8080	80.80%
CYP inhibitory promiscuity	-	0.9209	92.09%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5316	53.16%
Eye corrosion	-	0.9709	97.09%
Eye irritation	-	0.9106	91.06%
Skin irritation	+	0.6600	66.00%
Skin corrosion	-	0.8561	85.61%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4839	48.39%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.6033	60.33%
skin sensitisation	+	0.5409	54.09%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6074	60.74%
Acute Oral Toxicity (c)	III	0.5514	55.14%
Estrogen receptor binding	-	0.5787	57.87%
Androgen receptor binding	+	0.5741	57.41%
Thyroid receptor binding	+	0.5293	52.93%
Glucocorticoid receptor binding	+	0.5789	57.89%
Aromatase binding	-	0.7272	72.72%
PPAR gamma	+	0.5297	52.97%
Honey bee toxicity	-	0.9099	90.99%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9599	95.99%

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	91.09%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.03%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.63%	100.00%
CHEMBL2581	P07339	Cathepsin D	85.57%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.26%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.35%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.45%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.93%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.82%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.65%	95.89%
CHEMBL4072	P07858	Cathepsin B	80.46%	93.67%

Plants that contains it

• Jatropha curcas

Cross-Links

• PubChem: 51002626
• LOTUS: LTS0170097
• wikiData: Q105010946