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

Details

• Internal ID: 8d46ee4f-ad1e-4f42-a71d-547d570ada57
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: 2-[(1S,2R,4R,4aR,6R,8R,8aS)-4-acetyloxy-8-benzoyloxy-1-(carboxymethyl)-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(=O)O)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(=O)O)C(C)(C)C(=O)O
• InChI: InChI=1S/C29H36O10/c1-7-27(5)14-18(39-23(33)17-11-9-8-10-12-17)22-28(6,15-21(31)32)19(26(3,4)25(35)36)13-20(38-16(2)30)29(22,37)24(27)34/h7-12,18-20,22,37H,1,13-15H2,2-6H3,(H,31,32)(H,35,36)/t18-,19+,20-,22-,27+,28+,29+/m1/s1
• InChI Key: PQXGERVTTWCROY-DOLKAYCPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₀
• Molecular Weight: 544.60 g/mol
• Exact Mass: 544.23084734 g/mol
• Topological Polar Surface Area (TPSA): 165.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.27
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9883	98.83%
Caco-2	-	0.7334	73.34%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7411	74.11%
OATP2B1 inhibitior	-	0.8523	85.23%
OATP1B1 inhibitior	+	0.8746	87.46%
OATP1B3 inhibitior	+	0.7895	78.95%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8455	84.55%
P-glycoprotein inhibitior	+	0.7462	74.62%
P-glycoprotein substrate	-	0.5158	51.58%
CYP3A4 substrate	+	0.6908	69.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8934	89.34%
CYP3A4 inhibition	+	0.6698	66.98%
CYP2C9 inhibition	-	0.8506	85.06%
CYP2C19 inhibition	-	0.7250	72.50%
CYP2D6 inhibition	-	0.9472	94.72%
CYP1A2 inhibition	-	0.7962	79.62%
CYP2C8 inhibition	+	0.6909	69.09%
CYP inhibitory promiscuity	-	0.9310	93.10%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.6840	68.40%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9053	90.53%
Skin irritation	-	0.5969	59.69%
Skin corrosion	-	0.9503	95.03%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7579	75.79%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.7434	74.34%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.4848	48.48%
Acute Oral Toxicity (c)	I	0.4228	42.28%
Estrogen receptor binding	+	0.6601	66.01%
Androgen receptor binding	+	0.6454	64.54%
Thyroid receptor binding	+	0.5797	57.97%
Glucocorticoid receptor binding	+	0.7179	71.79%
Aromatase binding	+	0.6086	60.86%
PPAR gamma	+	0.5844	58.44%
Honey bee toxicity	-	0.7233	72.33%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
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	97.23%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.47%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.26%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.28%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.25%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.83%	94.62%
CHEMBL221	P23219	Cyclooxygenase-1	90.09%	90.17%
CHEMBL1951	P21397	Monoamine oxidase A	88.82%	91.49%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.48%	97.25%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.97%	94.08%
CHEMBL340	P08684	Cytochrome P450 3A4	87.72%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.92%	96.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.89%	85.14%
CHEMBL5028	O14672	ADAM10	84.04%	97.50%
CHEMBL2996	Q05655	Protein kinase C delta	83.64%	97.79%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.55%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.65%	91.07%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.23%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.38%	97.09%
CHEMBL1902	P62942	FK506-binding protein 1A	80.60%	97.05%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Cenchrus americanus
• Chlorophytum malayense
• Clausena indica
• Empetrum nigrum
• Ephedra lomatolepis
• Euonymus maackii
• Gentiana olivieri
• Jateorhiza palmata
• Lindera umbellata
• Morus notabilis
• Nicotiana gossei
• Orthosiphon aristatus var. aristatus
• Picradeniopsis oppositifolia
• Pinus halepensis
• Pinus thunbergii
• Pterocaulon rugosum
• Rauvolfia tetraphylla
• Salvia prionitis
• Satureja montana
• Saussurea triangulata
• Senecio grandiflorus
• Stephania succifera
• Stevia salicifolia
• Tetraria capillaris
• Teucrium alyssifolium
• Vernonanthura serratuloides
• Zephyranthes carinata

Cross-Links

• PubChem: 15548710
• NPASS: NPC129546
• LOTUS: LTS0021119
• wikiData: Q105213528