octanoic acid [(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-(2-methyl-1-oxobut-2-enoxy)-2-oxo-4-(1-oxobutoxy)-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] ester

Details

• Internal ID: 983f1670-d3f1-4d5d-a726-83cd70b1210d
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-(2-methylbut-2-enoyloxy)-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] octanoate
• SMILES (Canonical): CCCCCCCC(=O)OC1C2C(=C(C1OC(=O)C(=CC)C)C)C3C(C(CC2(C)OC(=O)C)OC(=O)CCC)(C(C(=O)O3)(C)O)O
• SMILES (Isomeric): CCCCCCCC(=O)O[C@H]1[C@H]2C(=C([C@@H]1OC(=O)C(=CC)C)C)[C@H]3[C@]([C@H](C[C@]2(C)OC(=O)C)OC(=O)CCC)([C@](C(=O)O3)(C)O)O
• InChI: InChI=1S/C34H50O12/c1-9-12-13-14-15-17-24(37)43-28-26-25(20(5)27(28)44-30(38)19(4)11-3)29-34(41,33(8,40)31(39)45-29)22(42-23(36)16-10-2)18-32(26,7)46-21(6)35/h11,22,26-29,40-41H,9-10,12-18H2,1-8H3/t22-,26+,27-,28-,29-,32-,33+,34+/m0/s1
• InChI Key: IXFPJGBNCFXKPI-LGJGSQFISA-N
• Popularity: 4,112 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₀O₁₂
• Molecular Weight: 650.80 g/mol
• Exact Mass: 650.33022703 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.93
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 13

Synonyms

• KBioGR_000221
• KBioSS_000221
• KBio2_000221
• KBio2_002789
• KBio2_005357
• KBio3_000441
• KBio3_000442
• Bio1_000202
• Bio1_000691
• Bio1_001180
• Bio2_000221
• Bio2_000701
• AKOS030242644
• AT23806
• Q27164929
• octanoic acid [(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-(2-methyl-1-oxobut-2-enoxy)-2-oxo-4-(1-oxobutoxy)-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9737	97.37%
Caco-2	-	0.7915	79.15%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7331	73.31%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.8356	83.56%
OATP1B3 inhibitior	+	0.8700	87.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9812	98.12%
P-glycoprotein inhibitior	+	0.8311	83.11%
P-glycoprotein substrate	+	0.9296	92.96%
CYP3A4 substrate	+	0.7008	70.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9059	90.59%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	+	0.8537	85.37%
CYP2C19 inhibition	+	0.8601	86.01%
CYP2D6 inhibition	-	0.9228	92.28%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	+	0.6185	61.85%
CYP inhibitory promiscuity	-	0.8693	86.93%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5505	55.05%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9116	91.16%
Skin irritation	+	0.5425	54.25%
Skin corrosion	-	0.9194	91.94%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5584	55.84%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8656	86.56%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5494	54.94%
Acute Oral Toxicity (c)	II	0.4100	41.00%
Estrogen receptor binding	+	0.7807	78.07%
Androgen receptor binding	+	0.7088	70.88%
Thyroid receptor binding	+	0.5182	51.82%
Glucocorticoid receptor binding	+	0.7977	79.77%
Aromatase binding	+	0.7557	75.57%
PPAR gamma	+	0.6723	67.23%
Honey bee toxicity	-	0.7698	76.98%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.7375	73.75%
Fish aquatic toxicity	+	0.9925	99.25%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293298	Q01453	Peripheral myelin protein 22	60.1 nM	Potency	via Super-PRED
CHEMBL3901	P16615	Sarcoplasmic/endoplasmic reticulum calcium ATPase 2	210 nM	IC50	via Super-PRED
CHEMBL2401	Q93084	Sarcoplasmic/endoplasmic reticulum calcium ATPase 3	210 nM	IC50	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	3.7 nM	Potency	via Super-PRED
CHEMBL1293256	P40225	Thrombopoietin	50.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.38%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.21%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.94%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.91%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.62%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	93.51%	97.79%
CHEMBL299	P17252	Protein kinase C alpha	92.44%	98.03%
CHEMBL2581	P07339	Cathepsin D	91.22%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.76%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	90.67%	92.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.86%	99.23%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.28%	95.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.63%	92.62%
CHEMBL230	P35354	Cyclooxygenase-2	87.16%	89.63%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.92%	93.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.77%	90.08%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.41%	86.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.79%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.14%	95.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.29%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.02%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.09%	95.89%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.06%	92.86%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.83%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.74%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.88%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	80.64%	91.19%
CHEMBL1937	Q92769	Histone deacetylase 2	80.59%	94.75%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	80.20%	85.94%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.17%	82.50%

Plants that contains it

• Thapsia garganica
• Thapsia villosa

Cross-Links

• PubChem: 49926
• LOTUS: LTS0031767
• wikiData: Q27164929