[(1S,2R,3E,5R,7R,8R,10S,13R)-13-acetyloxy-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxo-5-tricyclo[9.3.1.14,8]hexadeca-3,11-dienyl] (E)-3-phenylprop-2-enoate

Details

• Internal ID: cbf09576-4f9e-4b96-8c4c-f0dfca37fbbf
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: [(1S,2R,3E,5R,7R,8R,10S,13R)-13-acetyloxy-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxo-5-tricyclo[9.3.1.14,8]hexadeca-3,11-dienyl] (E)-3-phenylprop-2-enoate
• SMILES (Canonical): CC1=C2C(C(=O)C3(CC(=CC(C(C2(C)C)CC1OC(=O)C)O)C(CC3O)OC(=O)C=CC4=CC=CC=C4)C)O
• SMILES (Isomeric): CC1=C2[C@@H](C(=O)[C@@]3(C/C(=C\[C@H]([C@H](C2(C)C)C[C@H]1OC(=O)C)O)/[C@@H](C[C@H]3O)OC(=O)/C=C/C4=CC=CC=C4)C)O
• InChI: InChI=1S/C31H38O8/c1-17-23(38-18(2)32)14-21-22(33)13-20-16-31(5,29(37)28(36)27(17)30(21,3)4)25(34)15-24(20)39-26(35)12-11-19-9-7-6-8-10-19/h6-13,21-25,28,33-34,36H,14-16H2,1-5H3/b12-11+,20-13+/t21-,22-,23-,24-,25-,28+,31-/m1/s1
• InChI Key: VMOOHFUGVODOEB-JSJDUWMLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₈O₈
• Molecular Weight: 538.60 g/mol
• Exact Mass: 538.25666817 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 3.30
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9944	99.44%
Caco-2	-	0.7972	79.72%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7922	79.22%
OATP2B1 inhibitior	-	0.7153	71.53%
OATP1B1 inhibitior	+	0.8332	83.32%
OATP1B3 inhibitior	-	0.2508	25.08%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9620	96.20%
P-glycoprotein inhibitior	+	0.8017	80.17%
P-glycoprotein substrate	+	0.5230	52.30%
CYP3A4 substrate	+	0.6906	69.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8852	88.52%
CYP3A4 inhibition	-	0.5488	54.88%
CYP2C9 inhibition	-	0.7674	76.74%
CYP2C19 inhibition	-	0.7753	77.53%
CYP2D6 inhibition	-	0.9143	91.43%
CYP1A2 inhibition	-	0.7290	72.90%
CYP2C8 inhibition	+	0.7673	76.73%
CYP inhibitory promiscuity	-	0.8734	87.34%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.5639	56.39%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9399	93.99%
Skin irritation	-	0.5630	56.30%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7403	74.03%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.5144	51.44%
skin sensitisation	-	0.6606	66.06%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7642	76.42%
Acute Oral Toxicity (c)	I	0.4428	44.28%
Estrogen receptor binding	+	0.8215	82.15%
Androgen receptor binding	+	0.6931	69.31%
Thyroid receptor binding	+	0.6238	62.38%
Glucocorticoid receptor binding	+	0.8577	85.77%
Aromatase binding	+	0.6235	62.35%
PPAR gamma	+	0.7513	75.13%
Honey bee toxicity	-	0.6654	66.54%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
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
CHEMBL4040	P28482	MAP kinase ERK2	99.12%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.17%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.71%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	96.36%	91.49%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	95.68%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.05%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.17%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.36%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.11%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.56%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	90.17%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.05%	85.14%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.57%	94.08%
CHEMBL5028	O14672	ADAM10	86.49%	97.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.09%	93.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.77%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.95%	96.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.23%	81.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.19%	94.45%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.01%	94.23%

Plants that contains it

• Taxus cuspidata

Cross-Links

• PubChem: 163190461
• LOTUS: LTS0011169
• wikiData: Q105289125