[(1R,2S,3R,4S,4aR,8R,8aR)-4-[(1S)-1-acetyloxy-2-(5-oxo-2H-furan-3-yl)ethyl]-1,3-dihydroxy-8a-(hydroxymethyl)-3,4-dimethylspiro[1,2,4a,5,6,7-hexahydronaphthalene-8,2'-oxirane]-2-yl] (2S)-2-methylbutanoate

Details

• Internal ID: 8359c993-4754-4ecf-beaf-0d50649ac0a9
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(1R,2S,3R,4S,4aR,8R,8aR)-4-[(1S)-1-acetyloxy-2-(5-oxo-2H-furan-3-yl)ethyl]-1,3-dihydroxy-8a-(hydroxymethyl)-3,4-dimethylspiro[1,2,4a,5,6,7-hexahydronaphthalene-8,2'-oxirane]-2-yl] (2S)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1C(C2(C(CCCC23CO3)C(C1(C)O)(C)C(CC4=CC(=O)OC4)OC(=O)C)CO)O
• SMILES (Isomeric): CC[C@H](C)C(=O)O[C@H]1[C@@H]([C@@]2([C@H](CCC[C@]23CO3)[C@@]([C@@]1(C)O)(C)[C@H](CC4=CC(=O)OC4)OC(=O)C)CO)O
• InChI: InChI=1S/C27H40O10/c1-6-15(2)23(32)37-22-21(31)27(13-28)18(8-7-9-26(27)14-35-26)24(4,25(22,5)33)19(36-16(3)29)10-17-11-20(30)34-12-17/h11,15,18-19,21-22,28,31,33H,6-10,12-14H2,1-5H3/t15-,18+,19-,21-,22-,24-,25-,26-,27-/m0/s1
• InChI Key: CASHICPLRUEDOE-UGTNTXROSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₁₀
• Molecular Weight: 524.60 g/mol
• Exact Mass: 524.26214747 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.43
• H-Bond Acceptor: 10
• 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	+	0.9383	93.83%
Caco-2	-	0.7171	71.71%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7755	77.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8407	84.07%
OATP1B3 inhibitior	+	0.9353	93.53%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.9035	90.35%
P-glycoprotein inhibitior	+	0.6226	62.26%
P-glycoprotein substrate	+	0.5449	54.49%
CYP3A4 substrate	+	0.6784	67.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8965	89.65%
CYP3A4 inhibition	-	0.5996	59.96%
CYP2C9 inhibition	-	0.7481	74.81%
CYP2C19 inhibition	-	0.8541	85.41%
CYP2D6 inhibition	-	0.9261	92.61%
CYP1A2 inhibition	-	0.8731	87.31%
CYP2C8 inhibition	+	0.5278	52.78%
CYP inhibitory promiscuity	-	0.7535	75.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4858	48.58%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9400	94.00%
Skin irritation	-	0.5237	52.37%
Skin corrosion	-	0.9381	93.81%
Ames mutagenesis	-	0.5607	56.07%
Human Ether-a-go-go-Related Gene inhibition	-	0.5118	51.18%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5802	58.02%
skin sensitisation	-	0.9149	91.49%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6354	63.54%
Acute Oral Toxicity (c)	III	0.4687	46.87%
Estrogen receptor binding	+	0.8387	83.87%
Androgen receptor binding	+	0.7537	75.37%
Thyroid receptor binding	-	0.6024	60.24%
Glucocorticoid receptor binding	+	0.7303	73.03%
Aromatase binding	+	0.7434	74.34%
PPAR gamma	+	0.6358	63.58%
Honey bee toxicity	-	0.7388	73.88%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9867	98.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.96%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.67%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.04%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	97.99%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.08%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.00%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.23%	96.77%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.46%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.20%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.80%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.55%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	89.42%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.32%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	87.11%	95.93%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.15%	92.62%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.93%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.37%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	85.32%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.95%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.41%	89.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.22%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.10%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.56%	96.61%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.09%	83.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.26%	97.14%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.93%	89.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.11%	100.00%

Plants that contains it

• Scutellaria caucasica

Cross-Links

• PubChem: 162998448
• LOTUS: LTS0048466
• wikiData: Q104951855