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

Details

• Internal ID: 731257b6-13e1-4ec7-a276-937c3f201ebf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,2S,4S,7R,8R,9S,10S,12S,13S,16R)-4,7,8-triacetyloxy-12,13-dihydroxy-5,9-dimethyl-2-prop-1-en-2-yl-15-oxatetracyclo[7.6.1.02,6.013,16]hexadec-5-en-10-yl] acetate
• SMILES (Canonical): CC1=C2C(C(C3(C(CC(C4(C3C(C2(CC1OC(=O)C)C(=C)C)OC4)O)O)OC(=O)C)C)OC(=O)C)OC(=O)C
• SMILES (Isomeric): CC1=C2[C@H]([C@@H]([C@@]3([C@H](C[C@@H]([C@@]4([C@H]3[C@@H]([C@@]2(C[C@@H]1OC(=O)C)C(=C)C)OC4)O)O)OC(=O)C)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C28H38O11/c1-12(2)27-10-18(36-14(4)29)13(3)21(27)22(38-16(6)31)24(39-17(7)32)26(8)20(37-15(5)30)9-19(33)28(34)11-35-25(27)23(26)28/h18-20,22-25,33-34H,1,9-11H2,2-8H3/t18-,19-,20-,22+,23-,24-,25-,26+,27-,28-/m0/s1
• InChI Key: CSPOLLZGSHHTPE-FHXYGPRBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₁₁
• Molecular Weight: 550.60 g/mol
• Exact Mass: 550.24141202 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9808	98.08%
Caco-2	-	0.7322	73.22%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7877	78.77%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.8987	89.87%
OATP1B3 inhibitior	+	0.9560	95.60%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6224	62.24%
P-glycoprotein inhibitior	+	0.7502	75.02%
P-glycoprotein substrate	+	0.5634	56.34%
CYP3A4 substrate	+	0.6852	68.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8679	86.79%
CYP3A4 inhibition	-	0.7293	72.93%
CYP2C9 inhibition	-	0.7777	77.77%
CYP2C19 inhibition	-	0.8576	85.76%
CYP2D6 inhibition	-	0.9497	94.97%
CYP1A2 inhibition	-	0.7401	74.01%
CYP2C8 inhibition	+	0.6821	68.21%
CYP inhibitory promiscuity	-	0.9706	97.06%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5990	59.90%
Eye corrosion	-	0.9835	98.35%
Eye irritation	-	0.8800	88.00%
Skin irritation	-	0.5779	57.79%
Skin corrosion	-	0.9271	92.71%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6391	63.91%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8172	81.72%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.5705	57.05%
Acute Oral Toxicity (c)	III	0.4007	40.07%
Estrogen receptor binding	+	0.7276	72.76%
Androgen receptor binding	+	0.6782	67.82%
Thyroid receptor binding	+	0.5242	52.42%
Glucocorticoid receptor binding	+	0.7027	70.27%
Aromatase binding	+	0.6424	64.24%
PPAR gamma	+	0.7308	73.08%
Honey bee toxicity	-	0.5642	56.42%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9907	99.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.40%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.09%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.60%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.03%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.24%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.69%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	88.54%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.14%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.70%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.67%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.54%	94.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.46%	97.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.81%	97.09%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.63%	82.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.16%	97.14%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.13%	94.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.45%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.40%	95.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.37%	96.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.15%	97.25%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.61%	81.11%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.25%	93.00%

Plants that contains it

• Achyranthes aspera var. indica
• Achyrocline tomentosa
• Alhagi maurorum
• Allium angulosum
• Anemonella thalictroides
• Erythrophleum chlorostachys
• Goniothalamus dolichocarpus
• Guettarda platypoda
• Helicia nilagirica
• Lessingianthus brevifolius
• Lobelia inflata
• Phaleria macrocarpa
• Pistacia chinensis
• Pulicaria insignis
• Shirakiopsis indica
• Taxus mairei
• Tecomella undulata

Cross-Links

• PubChem: 10918656
• NPASS: NPC149423
• LOTUS: LTS0114314
• wikiData: Q104969489