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

Details

• Internal ID: e435de09-0b82-42a9-ade6-f80cf42f1e6f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4S,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-7,10-diacetyloxy-5-benzoyloxy-2-ethenyl-3,6,10a-trihydroxy-2,4b,8,8-tetramethyl-1-oxo-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-yl] benzoate
• SMILES (Canonical): CC(=O)OC1CC2C(C(C(C(C2(C3C1(C(=O)C(C(C3OC(=O)C4=CC=CC=C4)O)(C)C=C)O)C)OC(=O)C5=CC=CC=C5)O)OC(=O)C)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@@]([C@@H]3[C@@]1(C(=O)[C@@]([C@@H]([C@H]3OC(=O)C4=CC=CC=C4)O)(C)C=C)O)([C@H]([C@H]([C@H](C2(C)C)OC(=O)C)O)OC(=O)C5=CC=CC=C5)C
• InChI: InChI=1S/C38H44O12/c1-8-36(6)29(42)27(49-32(43)22-15-11-9-12-16-22)28-37(7)24(19-25(47-20(2)39)38(28,46)34(36)45)35(4,5)30(48-21(3)40)26(41)31(37)50-33(44)23-17-13-10-14-18-23/h8-18,24-31,41-42,46H,1,19H2,2-7H3/t24-,25+,26-,27-,28+,29+,30+,31-,36-,37-,38-/m0/s1
• InChI Key: UVLMOXBOUWFDIG-PQEFSWHNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₄O₁₂
• Molecular Weight: 692.70 g/mol
• Exact Mass: 692.28327683 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.21
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	-	0.8204	82.04%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7627	76.27%
OATP2B1 inhibitior	-	0.7126	71.26%
OATP1B1 inhibitior	+	0.8636	86.36%
OATP1B3 inhibitior	+	0.8260	82.60%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9545	95.45%
P-glycoprotein inhibitior	+	0.8225	82.25%
P-glycoprotein substrate	-	0.6465	64.65%
CYP3A4 substrate	+	0.6812	68.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	-	0.5999	59.99%
CYP2C9 inhibition	-	0.8640	86.40%
CYP2C19 inhibition	-	0.8823	88.23%
CYP2D6 inhibition	-	0.9312	93.12%
CYP1A2 inhibition	-	0.8078	80.78%
CYP2C8 inhibition	+	0.7215	72.15%
CYP inhibitory promiscuity	-	0.9342	93.42%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Non-required	0.5822	58.22%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.8968	89.68%
Skin irritation	-	0.7421	74.21%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6740	67.40%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.6041	60.41%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6649	66.49%
Estrogen receptor binding	+	0.7613	76.13%
Androgen receptor binding	+	0.6632	66.32%
Thyroid receptor binding	+	0.6472	64.72%
Glucocorticoid receptor binding	+	0.7198	71.98%
Aromatase binding	+	0.6066	60.66%
PPAR gamma	+	0.7245	72.45%
Honey bee toxicity	-	0.6933	69.33%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.61%	91.49%
CHEMBL221	P23219	Cyclooxygenase-1	96.83%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.12%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.38%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.76%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.49%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.20%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	92.19%	83.82%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.49%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	87.20%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.84%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.09%	95.89%
CHEMBL5028	O14672	ADAM10	85.94%	97.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.82%	94.08%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.71%	95.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.90%	94.62%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.40%	83.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.08%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.63%	89.00%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	80.57%	91.43%

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: 44583688
• NPASS: NPC26033
• ChEMBL: CHEMBL508513
• LOTUS: LTS0061063
• wikiData: Q105279950