Vesiculosin

Details

• Internal ID: 42683791-11ff-4b94-8835-fdd7374b6be0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Rhamnofolane and daphnane diterpenoids
• IUPAC Name: [5,6,11,14-tetrahydroxy-4-(hydroxymethyl)-8,12-dimethyl-7-oxo-14-prop-1-en-2-yl-3-oxatetracyclo[9.4.0.02,4.06,10]pentadec-8-en-15-yl] (2E,4E)-deca-2,4-dienoate
• SMILES (Canonical): CCCCCC=CC=CC(=O)OC1C2C3C(O3)(C(C4(C(C2(C(CC1(C(=C)C)O)C)O)C=C(C4=O)C)O)O)CO
• SMILES (Isomeric): CCCCC/C=C/C=C/C(=O)OC1C2C3C(O3)(C(C4(C(C2(C(CC1(C(=C)C)O)C)O)C=C(C4=O)C)O)O)CO
• InChI: InChI=1S/C30H42O9/c1-6-7-8-9-10-11-12-13-21(32)38-24-22-25-28(16-31,39-25)26(34)30(37)20(14-18(4)23(30)33)29(22,36)19(5)15-27(24,35)17(2)3/h10-14,19-20,22,24-26,31,34-37H,2,6-9,15-16H2,1,3-5H3/b11-10+,13-12+
• InChI Key: GTNHSMYOEDNTOZ-AQASXUMVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₂O₉
• Molecular Weight: 546.60 g/mol
• Exact Mass: 546.28288291 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 1.67
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

• 96935-20-5
• [5,6,11,14-tetrahydroxy-4-(hydroxymethyl)-8,12-dimethyl-7-oxo-14-prop-1-en-2-yl-3-oxatetracyclo[9.4.0.02,4.06,10]pentadec-8-en-15-yl] (2E,4E)-deca-2,4-dienoate
• (5,6,11,14-tetrahydroxy-4-(hydroxymethyl)-8,12-dimethyl-7-oxo-14-prop-1-en-2-yl-3-oxatetracyclo(9.4.0.02,4.06,10)pentadec-8-en-15-yl) (2E,4E)-deca-2,4-dienoate
• RefChem:194149
• 2,4-Decadienoic acid, 1,2,3,4,4a,4b,5a,6,6a,7,9a,9b-dodecahydro-3,6,6a,9b-tetrahydroxy-5a-(hydroxymethyl)-1,8-dimethyl-3-(1-methylethenyl)-7-oxobenz(7,8)azuleno(5,6-b)oxiren-4-yl ester, (1R-(1alpha,3alpha,4alpha,4abeta,4bbeta,5abeta,6beta,6a))
• NSC374342
• NSC-374342
• VESCULOSIN (B671071K103)
• B671071K103
• 2,4-Decadienoic acid, 1,2,3,4,4a,4b,5a,6,6a,7,9a,9b-dodecahydro-3,6,6a,9b-tetrahydroxy-5a-(hydroxymethyl)-1,8-dimethyl-3-(1-methylethenyl)-7-oxobenz(7,8)azuleno(5,6-b)oxiren-4-yl ester, (1R-(1alpha,3alpha,4alpha,4abeta,4bbeta,5abeta,6beta,6abeta,9aalpha,9balpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9101	91.01%
Caco-2	-	0.8007	80.07%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6280	62.80%
OATP2B1 inhibitior	-	0.8615	86.15%
OATP1B1 inhibitior	+	0.8144	81.44%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6318	63.18%
BSEP inhibitior	+	0.5661	56.61%
P-glycoprotein inhibitior	+	0.6772	67.72%
P-glycoprotein substrate	+	0.6392	63.92%
CYP3A4 substrate	+	0.7059	70.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8963	89.63%
CYP3A4 inhibition	+	0.6051	60.51%
CYP2C9 inhibition	+	0.5312	53.12%
CYP2C19 inhibition	-	0.7885	78.85%
CYP2D6 inhibition	-	0.9212	92.12%
CYP1A2 inhibition	-	0.7847	78.47%
CYP2C8 inhibition	+	0.6789	67.89%
CYP inhibitory promiscuity	-	0.8790	87.90%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6764	67.64%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9178	91.78%
Skin irritation	-	0.5481	54.81%
Skin corrosion	-	0.9265	92.65%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7966	79.66%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.5222	52.22%
skin sensitisation	-	0.8736	87.36%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.4858	48.58%
Acute Oral Toxicity (c)	III	0.5278	52.78%
Estrogen receptor binding	+	0.6924	69.24%
Androgen receptor binding	+	0.6933	69.33%
Thyroid receptor binding	+	0.5742	57.42%
Glucocorticoid receptor binding	+	0.6767	67.67%
Aromatase binding	+	0.6794	67.94%
PPAR gamma	-	0.4868	48.68%
Honey bee toxicity	-	0.8103	81.03%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5702	57.02%
Fish aquatic toxicity	+	0.9775	97.75%

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	97.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.03%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.16%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.90%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.86%	86.33%
CHEMBL230	P35354	Cyclooxygenase-2	93.82%	89.63%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.84%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.73%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.02%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	89.99%	94.73%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	89.71%	92.32%
CHEMBL2996	Q05655	Protein kinase C delta	88.63%	97.79%
CHEMBL299	P17252	Protein kinase C alpha	88.26%	98.03%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.88%	94.80%
CHEMBL221	P23219	Cyclooxygenase-1	87.10%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.63%	97.09%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.62%	96.90%
CHEMBL340	P08684	Cytochrome P450 3A4	86.05%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.93%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.45%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.42%	93.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.90%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.96%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.30%	89.34%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.98%	91.24%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.85%	96.47%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.66%	100.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.30%	95.71%

Plants that contains it

• Diarthron vesiculosum

Cross-Links

• PubChem: 5477990
• LOTUS: LTS0220703
• wikiData: Q105019099