[(1R,3R,4R,4aS,7S,8aS)-4-hydroxy-3,4a,8,8-tetramethyl-4-[2-(5-oxo-2H-furan-4-yl)ethyl]-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate

Details

• Internal ID: 464944e2-467e-45b0-abe6-3175118eaf4b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(1R,3R,4R,4aS,7S,8aS)-4-hydroxy-3,4a,8,8-tetramethyl-4-[2-(5-oxo-2H-furan-4-yl)ethyl]-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate
• InChI: InChI=1S/C28H44O11/c1-14-12-17(37-15(2)30)23-26(3,4)19(39-25-22(33)21(32)20(31)18(13-29)38-25)7-9-27(23,5)28(14,35)10-6-16-8-11-36-24(16)34/h8,14,17-23,25,29,31-33,35H,6-7,9-13H2,1-5H3/t14-,17-,18-,19+,20-,21+,22-,23+,25+,27+,28-/m1/s1
• InChI Key: CFZLMOHGTWAPSR-YKWMLKEFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₄O₁₁
• Molecular Weight: 556.60 g/mol
• Exact Mass: 556.28836222 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.58
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7917	79.17%
Caco-2	-	0.8378	83.78%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8458	84.58%
OATP2B1 inhibitior	-	0.5767	57.67%
OATP1B1 inhibitior	+	0.8183	81.83%
OATP1B3 inhibitior	+	0.8881	88.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.6170	61.70%
P-glycoprotein inhibitior	+	0.5811	58.11%
P-glycoprotein substrate	-	0.5908	59.08%
CYP3A4 substrate	+	0.7133	71.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9029	90.29%
CYP3A4 inhibition	-	0.8360	83.60%
CYP2C9 inhibition	-	0.8351	83.51%
CYP2C19 inhibition	-	0.9177	91.77%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	-	0.9135	91.35%
CYP2C8 inhibition	+	0.5988	59.88%
CYP inhibitory promiscuity	-	0.9470	94.70%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5431	54.31%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9288	92.88%
Skin irritation	-	0.5151	51.51%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4444	44.44%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9076	90.76%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5726	57.26%
Acute Oral Toxicity (c)	I	0.4634	46.34%
Estrogen receptor binding	+	0.6921	69.21%
Androgen receptor binding	+	0.6834	68.34%
Thyroid receptor binding	-	0.5338	53.38%
Glucocorticoid receptor binding	+	0.6332	63.32%
Aromatase binding	+	0.7247	72.47%
PPAR gamma	+	0.6354	63.54%
Honey bee toxicity	-	0.6896	68.96%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9655	96.55%

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	98.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.36%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.76%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.36%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.28%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	94.05%	97.79%
CHEMBL2581	P07339	Cathepsin D	91.87%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.67%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.28%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.92%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.70%	97.33%
CHEMBL1937	Q92769	Histone deacetylase 2	83.95%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.67%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	83.50%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.29%	99.23%
CHEMBL5028	O14672	ADAM10	82.06%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	80.49%	92.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.41%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.08%	97.14%

Plants that contains it

• Vitex rotundifolia

Cross-Links

• PubChem: 10769138
• LOTUS: LTS0147593
• wikiData: Q104957310