[(2S,3S,4R,4aS,4bS,5R,7R,8aR,9R,10aS)-2,3-diacetyloxy-7-ethenyl-5,8a,9-trihydroxy-1,1,4a,7-tetramethyl-8-oxo-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthren-4-yl] benzoate

Details

• Internal ID: ad88e88c-4be9-4776-a03d-c0ff92683413
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4R,4aS,4bS,5R,7R,8aR,9R,10aS)-2,3-diacetyloxy-7-ethenyl-5,8a,9-trihydroxy-1,1,4a,7-tetramethyl-8-oxo-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthren-4-yl] benzoate
• SMILES (Canonical): CC(=O)OC1C(C(C2CC(C3(C(C2(C1OC(=O)C4=CC=CC=C4)C)C(CC(C3=O)(C)C=C)O)O)O)(C)C)OC(=O)C
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@@H]([C@]2([C@@H](C[C@H]([C@@]3([C@@H]2[C@@H](C[C@](C3=O)(C)C=C)O)O)O)C([C@@H]1OC(=O)C)(C)C)C)OC(=O)C4=CC=CC=C4
• InChI: InChI=1S/C31H40O10/c1-8-29(6)15-19(34)23-30(7)20(14-21(35)31(23,38)27(29)37)28(4,5)24(40-17(3)33)22(39-16(2)32)25(30)41-26(36)18-12-10-9-11-13-18/h8-13,19-25,34-35,38H,1,14-15H2,2-7H3/t19-,20+,21-,22+,23-,24-,25+,29+,30+,31+/m1/s1
• InChI Key: HVCLVVFTATWQBZ-SRHIYTGZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₀O₁₀
• Molecular Weight: 572.60 g/mol
• Exact Mass: 572.26214747 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9582	95.82%
Caco-2	-	0.7928	79.28%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6253	62.53%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8598	85.98%
OATP1B3 inhibitior	+	0.8842	88.42%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9054	90.54%
P-glycoprotein inhibitior	+	0.7465	74.65%
P-glycoprotein substrate	-	0.6225	62.25%
CYP3A4 substrate	+	0.6796	67.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8702	87.02%
CYP3A4 inhibition	+	0.6630	66.30%
CYP2C9 inhibition	-	0.8643	86.43%
CYP2C19 inhibition	-	0.8646	86.46%
CYP2D6 inhibition	-	0.9228	92.28%
CYP1A2 inhibition	-	0.7859	78.59%
CYP2C8 inhibition	+	0.6200	62.00%
CYP inhibitory promiscuity	-	0.9500	95.00%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.6166	61.66%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9036	90.36%
Skin irritation	-	0.6406	64.06%
Skin corrosion	-	0.9110	91.10%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7613	76.13%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5390	53.90%
skin sensitisation	-	0.6931	69.31%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7445	74.45%
Acute Oral Toxicity (c)	III	0.6386	63.86%
Estrogen receptor binding	+	0.7332	73.32%
Androgen receptor binding	+	0.6658	66.58%
Thyroid receptor binding	+	0.5807	58.07%
Glucocorticoid receptor binding	+	0.6710	67.10%
Aromatase binding	+	0.6382	63.82%
PPAR gamma	+	0.6531	65.31%
Honey bee toxicity	-	0.6721	67.21%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9971	99.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.23%	91.49%
CHEMBL221	P23219	Cyclooxygenase-1	98.04%	90.17%
CHEMBL240	Q12809	HERG	96.85%	89.76%
CHEMBL2581	P07339	Cathepsin D	96.17%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.17%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	94.30%	94.62%
CHEMBL340	P08684	Cytochrome P450 3A4	93.09%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.27%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.16%	82.69%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.12%	91.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.95%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.81%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.22%	96.95%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.15%	94.08%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.81%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.47%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.22%	91.07%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.76%	93.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.22%	97.21%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.87%	83.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.34%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.71%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.59%	89.00%
CHEMBL4208	P20618	Proteasome component C5	80.52%	90.00%
CHEMBL5028	O14672	ADAM10	80.32%	97.50%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Asplenium nidus
• Astragalus laxmannii subsp. laxmannii
• Celmisia petriei
• Cenchrus americanus
• Chlorophytum malayense
• Cirsium helenioides
• Clausena indica
• Clusia torresii
• Empetrum nigrum
• Ephedra lomatolepis
• Euonymus maackii
• Ferula assa-foetida
• Gentiana olivieri
• Handroanthus guayacan
• Jateorhiza palmata
• Lindera umbellata
• Morus notabilis
• Nicotiana gossei
• Orthosiphon aristatus
• Orthosiphon aristatus var. aristatus
• Oryza sativa
• Picradeniopsis oppositifolia
• Pinus halepensis
• Pinus thunbergii
• Populus tremula
• Primula veris
• Pterocaulon rugosum
• Rauvolfia tetraphylla
• Salvia prionitis
• Satureja montana
• Saussurea triangulata
• Senecio grandiflorus
• Senecio integerrimus
• Stephania succifera
• Stevia salicifolia
• Tetraria capillaris
• Teucrium alyssifolium
• Ulmus laciniata
• Vernonanthura serratuloides
• Zephyranthes carinata

Cross-Links

• PubChem: 10076785
• NPASS: NPC250046
• LOTUS: LTS0001123
• wikiData: Q105034186