[(1R,2S,3R,4R,4aS,7S,8aR)-2-benzoyloxy-3,7-dihydroxy-3,4,8a-trimethyl-8-methylidene-4-[(E)-2-(5-oxo-2H-furan-3-yl)ethenyl]-1,2,4a,5,6,7-hexahydronaphthalen-1-yl] benzoate

Details

• Internal ID: 1068c2e0-6837-4480-b216-66c5a00d62f0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1R,2S,3R,4R,4aS,7S,8aR)-2-benzoyloxy-3,7-dihydroxy-3,4,8a-trimethyl-8-methylidene-4-[(E)-2-(5-oxo-2H-furan-3-yl)ethenyl]-1,2,4a,5,6,7-hexahydronaphthalen-1-yl] benzoate
• SMILES (Canonical): CC1(C2CCC(C(=C)C2(C(C(C1(C)O)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)C)O)C=CC5=CC(=O)OC5
• SMILES (Isomeric): C[C@]1([C@H]2CC[C@@H](C(=C)[C@@]2([C@H]([C@@H]([C@]1(C)O)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)C)O)/C=C/C5=CC(=O)OC5
• InChI: InChI=1S/C34H36O8/c1-21-25(35)15-16-26-32(2,18-17-22-19-27(36)40-20-22)34(4,39)29(42-31(38)24-13-9-6-10-14-24)28(33(21,26)3)41-30(37)23-11-7-5-8-12-23/h5-14,17-19,25-26,28-29,35,39H,1,15-16,20H2,2-4H3/b18-17+/t25-,26+,28-,29-,32+,33-,34-/m0/s1
• InChI Key: INDRXXKQJAKWRM-OMAAXZSASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₃₆O₈
• Molecular Weight: 572.60 g/mol
• Exact Mass: 572.24101810 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.58
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9766	97.66%
Caco-2	-	0.8026	80.26%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7550	75.50%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8675	86.75%
OATP1B3 inhibitior	+	0.8930	89.30%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7021	70.21%
BSEP inhibitior	+	0.8817	88.17%
P-glycoprotein inhibitior	+	0.8420	84.20%
P-glycoprotein substrate	-	0.5801	58.01%
CYP3A4 substrate	+	0.6806	68.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.6073	60.73%
CYP2C9 inhibition	-	0.7015	70.15%
CYP2C19 inhibition	-	0.8004	80.04%
CYP2D6 inhibition	-	0.9085	90.85%
CYP1A2 inhibition	-	0.6038	60.38%
CYP2C8 inhibition	+	0.7102	71.02%
CYP inhibitory promiscuity	-	0.7987	79.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5166	51.66%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9137	91.37%
Skin irritation	-	0.5958	59.58%
Skin corrosion	-	0.9124	91.24%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7466	74.66%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.5926	59.26%
skin sensitisation	-	0.8124	81.24%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5304	53.04%
Acute Oral Toxicity (c)	III	0.4476	44.76%
Estrogen receptor binding	+	0.8218	82.18%
Androgen receptor binding	+	0.7258	72.58%
Thyroid receptor binding	+	0.6461	64.61%
Glucocorticoid receptor binding	+	0.8260	82.60%
Aromatase binding	+	0.6281	62.81%
PPAR gamma	+	0.6292	62.92%
Honey bee toxicity	-	0.8098	80.98%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5251	52.51%
Fish aquatic toxicity	+	0.9918	99.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.31%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.69%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	94.62%	90.17%
CHEMBL1951	P21397	Monoamine oxidase A	94.51%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.47%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.43%	95.56%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.84%	83.00%
CHEMBL5028	O14672	ADAM10	86.65%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	85.54%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.36%	100.00%
CHEMBL2535	P11166	Glucose transporter	83.35%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.06%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.85%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.74%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.25%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.10%	96.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.58%	93.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.18%	97.14%

Plants that contains it

• Scutellaria barbata

Cross-Links

• PubChem: 122177463
• LOTUS: LTS0053818
• wikiData: Q105116121