[(1R,2R,3S,4S,5S,7R,9S,10R,11R,13S)-2,7,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxo-4-tetracyclo[7.6.0.03,7.010,13]pentadecanyl] (E)-3-phenylprop-2-enoate

Details

• Internal ID: be287d38-9fe9-4bbf-b2ec-36aa238fcd53
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: [(1R,2R,3S,4S,5S,7R,9S,10R,11R,13S)-2,7,11-trihydroxy-1,5,9,12,12-pentamethyl-8-oxo-4-tetracyclo[7.6.0.03,7.010,13]pentadecanyl] (E)-3-phenylprop-2-enoate
• SMILES (Canonical): CC1CC2(C(C1OC(=O)C=CC3=CC=CC=C3)C(C4(CCC5C(C4(C2=O)C)C(C5(C)C)O)C)O)O
• SMILES (Isomeric): C[C@H]1C[C@]2([C@H]([C@H]1OC(=O)/C=C/C3=CC=CC=C3)[C@H]([C@@]4(CC[C@H]5[C@H]([C@@]4(C2=O)C)[C@H](C5(C)C)O)C)O)O
• InChI: InChI=1S/C29H38O6/c1-16-15-29(34)21(22(16)35-19(30)12-11-17-9-7-6-8-10-17)24(32)27(4)14-13-18-20(23(31)26(18,2)3)28(27,5)25(29)33/h6-12,16,18,20-24,31-32,34H,13-15H2,1-5H3/b12-11+/t16-,18-,20-,21+,22-,23+,24+,27-,28+,29+/m0/s1
• InChI Key: ZPRFHHPYSLMQTE-AWZHKKSRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₈O₆
• Molecular Weight: 482.60 g/mol
• Exact Mass: 482.26683893 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.38
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9732	97.32%
Caco-2	-	0.8044	80.44%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6965	69.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8532	85.32%
OATP1B3 inhibitior	+	0.8613	86.13%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	+	0.7137	71.37%
P-glycoprotein inhibitior	-	0.4464	44.64%
P-glycoprotein substrate	-	0.6689	66.89%
CYP3A4 substrate	+	0.6947	69.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8911	89.11%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.7397	73.97%
CYP2C19 inhibition	-	0.7927	79.27%
CYP2D6 inhibition	-	0.9325	93.25%
CYP1A2 inhibition	-	0.7151	71.51%
CYP2C8 inhibition	+	0.6823	68.23%
CYP inhibitory promiscuity	-	0.8917	89.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5589	55.89%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9403	94.03%
Skin irritation	-	0.5206	52.06%
Skin corrosion	-	0.8856	88.56%
Ames mutagenesis	-	0.7970	79.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7132	71.32%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5323	53.23%
skin sensitisation	-	0.7881	78.81%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8258	82.58%
Acute Oral Toxicity (c)	III	0.4250	42.50%
Estrogen receptor binding	+	0.7891	78.91%
Androgen receptor binding	+	0.7530	75.30%
Thyroid receptor binding	+	0.6567	65.67%
Glucocorticoid receptor binding	+	0.7012	70.12%
Aromatase binding	+	0.7383	73.83%
PPAR gamma	+	0.6046	60.46%
Honey bee toxicity	-	0.7867	78.67%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9898	98.98%

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	97.82%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.27%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.53%	95.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	92.04%	94.08%
CHEMBL221	P23219	Cyclooxygenase-1	91.94%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.64%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.45%	93.99%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	88.49%	94.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.11%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.21%	95.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.83%	94.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.83%	91.07%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.40%	82.69%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.39%	93.00%
CHEMBL2581	P07339	Cathepsin D	84.87%	98.95%
CHEMBL5028	O14672	ADAM10	84.85%	97.50%
CHEMBL4040	P28482	MAP kinase ERK2	82.36%	83.82%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.24%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.08%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.31%	97.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.08%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.69%	94.75%

Plants that contains it

• Euphorbia micractina

Cross-Links

• PubChem: 73350454
• NPASS: NPC202093