[(2S,3S,4R,5R,6S)-6-[(3R)-5-[(1R,3R,4aS,8aS)-3-hydroperoxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl] acetate

Details

• Internal ID: 06aa6078-6ea1-42f0-bbc5-acc1a0953eaa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4R,5R,6S)-6-[(3R)-5-[(1R,3R,4aS,8aS)-3-hydroperoxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-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)(CCC2C(=C)C(CC3C2(CCCC3(C)C)C)OO)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)(CC[C@H]2C(=C)[C@@H](C[C@@H]3[C@@]2(CCCC3(C)C)C)OO)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/h9,17,19-25,30-32H,1-2,10-15H2,3-8H3/t17-,19-,20+,21-,22+,23+,24+,25-,27-,28+/m0/s1
• InChI Key: YBFOIUOGGJEULY-AXNAUFRVSA-N
• Popularity: 0 references 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: 3.90
• Atomic LogP (AlogP): 4.39
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9287	92.87%
Caco-2	-	0.7780	77.80%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6240	62.40%
OATP2B1 inhibitior	-	0.7146	71.46%
OATP1B1 inhibitior	+	0.8018	80.18%
OATP1B3 inhibitior	+	0.7924	79.24%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5710	57.10%
P-glycoprotein inhibitior	+	0.6056	60.56%
P-glycoprotein substrate	-	0.5784	57.84%
CYP3A4 substrate	+	0.7080	70.80%
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	+	0.6360	63.60%
CYP inhibitory promiscuity	-	0.9112	91.12%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6895	68.95%
Eye corrosion	-	0.9859	98.59%
Eye irritation	-	0.9304	93.04%
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	+	0.6553	65.53%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5673	56.73%
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	-	0.5970	59.70%
Acute Oral Toxicity (c)	III	0.4830	48.30%
Estrogen receptor binding	+	0.5905	59.05%
Androgen receptor binding	+	0.6014	60.14%
Thyroid receptor binding	-	0.4903	49.03%
Glucocorticoid receptor binding	+	0.6134	61.34%
Aromatase binding	+	0.6909	69.09%
PPAR gamma	+	0.5527	55.27%
Honey bee toxicity	-	0.6556	65.56%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.72%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.18%	97.25%
CHEMBL2581	P07339	Cathepsin D	94.34%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.38%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.28%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.45%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.31%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.03%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.45%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	84.54%	94.73%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.22%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.45%	95.56%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.27%	82.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.21%	89.50%
CHEMBL5028	O14672	ADAM10	82.80%	97.50%
CHEMBL233	P35372	Mu opioid receptor	82.78%	97.93%
CHEMBL340	P08684	Cytochrome P450 3A4	82.77%	91.19%
CHEMBL1977	P11473	Vitamin D receptor	82.75%	99.43%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.08%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.38%	97.36%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.83%	95.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.66%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.56%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.29%	98.75%

Plants that contains it

• Aster spathulifolius

Cross-Links

• PubChem: 10481452
• LOTUS: LTS0071172
• wikiData: Q105345804