2-[(1S,2R,4R,4aR,6R,8R,8aS)-4-acetyloxy-8-benzoyloxy-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-2,3,4,7,8,8a-hexahydronaphthalen-2-yl]-2-methylpropanoic acid

Details

• Internal ID: fcc39653-39cb-4695-8732-3841b4fb95b2
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Benzoic acid esters
• IUPAC Name: 2-[(1S,2R,4R,4aR,6R,8R,8aS)-4-acetyloxy-8-benzoyloxy-1-(cyanomethyl)-6-ethenyl-4a-hydroxy-1,6-dimethyl-5-oxo-2,3,4,7,8,8a-hexahydronaphthalen-2-yl]-2-methylpropanoic acid
• SMILES (Canonical): CC(=O)OC1CC(C(C2C1(C(=O)C(CC2OC(=O)C3=CC=CC=C3)(C)C=C)O)(C)CC#N)C(C)(C)C(=O)O
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@H]([C@]([C@@H]2[C@@]1(C(=O)[C@@](C[C@H]2OC(=O)C3=CC=CC=C3)(C)C=C)O)(C)CC#N)C(C)(C)C(=O)O
• InChI: InChI=1S/C29H35NO8/c1-7-27(5)16-19(38-23(32)18-11-9-8-10-12-18)22-28(6,13-14-30)20(26(3,4)25(34)35)15-21(37-17(2)31)29(22,36)24(27)33/h7-12,19-22,36H,1,13,15-16H2,2-6H3,(H,34,35)/t19-,20+,21-,22-,27+,28+,29+/m1/s1
• InChI Key: MPPSSZWVJZPPHO-LGWYJBSXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₅NO₈
• Molecular Weight: 525.60 g/mol
• Exact Mass: 525.23626707 g/mol
• Topological Polar Surface Area (TPSA): 151.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.71
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9861	98.61%
Caco-2	-	0.7705	77.05%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6330	63.30%
OATP2B1 inhibitior	-	0.7169	71.69%
OATP1B1 inhibitior	+	0.8757	87.57%
OATP1B3 inhibitior	+	0.8180	81.80%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8970	89.70%
P-glycoprotein inhibitior	+	0.7505	75.05%
P-glycoprotein substrate	-	0.5370	53.70%
CYP3A4 substrate	+	0.7025	70.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8879	88.79%
CYP3A4 inhibition	+	0.7128	71.28%
CYP2C9 inhibition	-	0.7844	78.44%
CYP2C19 inhibition	-	0.7436	74.36%
CYP2D6 inhibition	-	0.9308	93.08%
CYP1A2 inhibition	-	0.7554	75.54%
CYP2C8 inhibition	+	0.7122	71.22%
CYP inhibitory promiscuity	-	0.8313	83.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.6671	66.71%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9218	92.18%
Skin irritation	-	0.6962	69.62%
Skin corrosion	-	0.9513	95.13%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6724	67.24%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.7939	79.39%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.6739	67.39%
Acute Oral Toxicity (c)	III	0.4655	46.55%
Estrogen receptor binding	+	0.6918	69.18%
Androgen receptor binding	+	0.6456	64.56%
Thyroid receptor binding	+	0.6459	64.59%
Glucocorticoid receptor binding	+	0.7509	75.09%
Aromatase binding	+	0.6931	69.31%
PPAR gamma	+	0.6246	62.46%
Honey bee toxicity	-	0.6277	62.77%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.90%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.36%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.82%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.41%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	92.97%	94.08%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.91%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.20%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.59%	96.95%
CHEMBL5028	O14672	ADAM10	88.17%	97.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.07%	97.25%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	86.96%	94.97%
CHEMBL221	P23219	Cyclooxygenase-1	86.88%	90.17%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.75%	94.23%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	85.53%	97.53%
CHEMBL2535	P11166	Glucose transporter	84.56%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.96%	95.50%
CHEMBL1951	P21397	Monoamine oxidase A	83.32%	91.49%
CHEMBL340	P08684	Cytochrome P450 3A4	82.45%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.22%	99.23%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Asplenium nidus
• Astragalus laxmannii subsp. laxmannii
• Catoferia spicata
• 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: 15548729
• NPASS: NPC9634
• LOTUS: LTS0221495
• wikiData: Q105169665