2-[(1S,2S,7R,8R,9S,10S,12S,13S,16R)-7,8,10-triacetyloxy-4,12,13-trihydroxy-5,9-dimethyl-15-oxatetracyclo[7.6.1.02,6.013,16]hexadec-4-en-2-yl]propan-2-yl benzoate

Details

• Internal ID: 9330fe00-0b98-4a2b-b2ad-056ea524cf01
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 2-[(1S,2S,7R,8R,9S,10S,12S,13S,16R)-7,8,10-triacetyloxy-4,12,13-trihydroxy-5,9-dimethyl-15-oxatetracyclo[7.6.1.02,6.013,16]hexadec-4-en-2-yl]propan-2-yl benzoate
• SMILES (Canonical): CC1=C(CC2(C1C(C(C3(C(CC(C4(C3C2OC4)O)O)OC(=O)C)C)OC(=O)C)OC(=O)C)C(C)(C)OC(=O)C5=CC=CC=C5)O
• SMILES (Isomeric): CC1=C(C[C@@]2(C1[C@H]([C@@H]([C@@]3([C@H](C[C@@H]([C@@]4([C@H]3[C@@H]2OC4)O)O)OC(=O)C)C)OC(=O)C)OC(=O)C)C(C)(C)OC(=O)C5=CC=CC=C5)O
• InChI: InChI=1S/C33H42O12/c1-16-21(37)14-32(30(5,6)45-29(39)20-11-9-8-10-12-20)24(16)25(43-18(3)35)27(44-19(4)36)31(7)23(42-17(2)34)13-22(38)33(40)15-41-28(32)26(31)33/h8-12,22-28,37-38,40H,13-15H2,1-7H3/t22-,23-,24?,25+,26-,27-,28-,31+,32-,33-/m0/s1
• InChI Key: JZKAGZRNVQGBOZ-VUJLEAODSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₂O₁₂
• Molecular Weight: 630.70 g/mol
• Exact Mass: 630.26762677 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9880	98.80%
Caco-2	-	0.8007	80.07%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8049	80.49%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8507	85.07%
OATP1B3 inhibitior	+	0.9278	92.78%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9392	93.92%
P-glycoprotein inhibitior	+	0.8108	81.08%
P-glycoprotein substrate	+	0.6297	62.97%
CYP3A4 substrate	+	0.6957	69.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8589	85.89%
CYP3A4 inhibition	-	0.6979	69.79%
CYP2C9 inhibition	-	0.6540	65.40%
CYP2C19 inhibition	-	0.7667	76.67%
CYP2D6 inhibition	-	0.9239	92.39%
CYP1A2 inhibition	-	0.6795	67.95%
CYP2C8 inhibition	+	0.8243	82.43%
CYP inhibitory promiscuity	-	0.9026	90.26%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5736	57.36%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9023	90.23%
Skin irritation	-	0.6845	68.45%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6651	66.51%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5822	58.22%
skin sensitisation	-	0.7770	77.70%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.4699	46.99%
Acute Oral Toxicity (c)	III	0.3659	36.59%
Estrogen receptor binding	+	0.7718	77.18%
Androgen receptor binding	+	0.7152	71.52%
Thyroid receptor binding	+	0.5842	58.42%
Glucocorticoid receptor binding	+	0.6955	69.55%
Aromatase binding	+	0.6819	68.19%
PPAR gamma	+	0.7248	72.48%
Honey bee toxicity	-	0.7419	74.19%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9969	99.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.38%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.36%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.47%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.31%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.59%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.17%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.73%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	87.90%	90.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.91%	97.14%
CHEMBL5028	O14672	ADAM10	86.82%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.26%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	85.83%	91.49%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.88%	93.04%
CHEMBL340	P08684	Cytochrome P450 3A4	84.47%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.22%	96.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.17%	95.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.75%	97.21%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.74%	93.56%
CHEMBL3401	O75469	Pregnane X receptor	81.54%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.11%	94.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.19%	81.11%

Plants that contains it

• Cota triumfetti
• Taxus mairei

Cross-Links

• PubChem: 101168102
• LOTUS: LTS0062690
• wikiData: Q105291320