[(13R)-7alpha-Hydroperoxylabda-8,14-diene-13-yl]4-O-acetyl-6-deoxy-alpha-L-idopyranoside

Details

• Internal ID: 431f7f31-61ed-4e3c-b587-4119621f2d90
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4R,5R,6S)-6-[(3R)-5-[(3R,4aS,8aS)-3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC(C)(CCC2=C(C(CC3C2(CCCC3(C)C)C)OO)C)C=C)O)O)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@](C)(CCC2=C([C@@H](C[C@@H]3[C@@]2(CCCC3(C)C)C)OO)C)C=C)O)O)OC(=O)C
• InChI: InChI=1S/C28H46O8/c1-9-27(7,35-25-23(31)22(30)24(17(3)33-25)34-18(4)29)14-11-19-16(2)20(36-32)15-21-26(5,6)12-10-13-28(19,21)8/h9,17,20-25,30-32H,1,10-15H2,2-8H3/t17-,20+,21-,22+,23+,24+,25-,27-,28+/m0/s1
• InChI Key: CYFQGASFWKNUEE-PEJODWCSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₆O₈
• Molecular Weight: 510.70 g/mol
• Exact Mass: 510.31926842 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.54
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• [(13R)-7alpha-Hydroperoxylabda-8,14-diene-13-yl]4-O-acetyl-6-deoxy-alpha-L-idopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9287	92.87%
Caco-2	-	0.7359	73.59%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6240	62.40%
OATP2B1 inhibitior	-	0.7166	71.66%
OATP1B1 inhibitior	+	0.8327	83.27%
OATP1B3 inhibitior	+	0.7924	79.24%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5072	50.72%
P-glycoprotein inhibitior	+	0.6609	66.09%
P-glycoprotein substrate	-	0.5323	53.23%
CYP3A4 substrate	+	0.7085	70.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8795	87.95%
CYP3A4 inhibition	-	0.6984	69.84%
CYP2C9 inhibition	-	0.7720	77.20%
CYP2C19 inhibition	-	0.7264	72.64%
CYP2D6 inhibition	-	0.9355	93.55%
CYP1A2 inhibition	-	0.6470	64.70%
CYP2C8 inhibition	+	0.6808	68.08%
CYP inhibitory promiscuity	-	0.9112	91.12%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6895	68.95%
Eye corrosion	-	0.9859	98.59%
Eye irritation	-	0.9274	92.74%
Skin irritation	-	0.5981	59.81%
Skin corrosion	-	0.9158	91.58%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4685	46.85%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5322	53.22%
skin sensitisation	-	0.7519	75.19%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7086	70.86%
Acute Oral Toxicity (c)	III	0.4830	48.30%
Estrogen receptor binding	+	0.5764	57.64%
Androgen receptor binding	+	0.5967	59.67%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6480	64.80%
Aromatase binding	+	0.7151	71.51%
PPAR gamma	-	0.4842	48.42%
Honey bee toxicity	-	0.6285	62.85%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9945	99.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.20%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.30%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.27%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.15%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.87%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.40%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.61%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	86.41%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.24%	96.61%
CHEMBL233	P35372	Mu opioid receptor	85.32%	97.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.25%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.14%	95.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.95%	100.00%
CHEMBL5028	O14672	ADAM10	84.70%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.64%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.24%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.05%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	81.54%	91.19%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.39%	82.50%
CHEMBL259	P32245	Melanocortin receptor 4	81.32%	95.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.18%	94.45%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.17%	96.90%

Plants that contains it

• Aster spathulifolius

Cross-Links

• PubChem: 11049491
• NPASS: NPC280991
• LOTUS: LTS0180863
• wikiData: Q104972279