(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one

Details

• Internal ID: 85f65d95-d91e-4deb-af2b-67a37879d11f
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
• SMILES (Canonical): CC12CCC(C(C1CCC(=C)C2CC=C3C(COC3=O)O)(C)COC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C[C@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2C/C=C/3\[C@@H](COC3=O)O)(C)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C26H40O10/c1-13-4-7-18-25(2,15(13)6-5-14-16(28)11-34-23(14)33)9-8-19(29)26(18,3)12-35-24-22(32)21(31)20(30)17(10-27)36-24/h5,15-22,24,27-32H,1,4,6-12H2,2-3H3/b14-5+/t15-,16-,17-,18+,19-,20-,21+,22-,24-,25-,26+/m1/s1
• InChI Key: VUEPOIYXKZTLMD-WDQPWUIFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₀O₁₀
• Molecular Weight: 512.60 g/mol
• Exact Mass: 512.26214747 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.21
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7469	74.69%
Caco-2	-	0.8212	82.12%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7735	77.35%
OATP2B1 inhibitior	-	0.5828	58.28%
OATP1B1 inhibitior	+	0.8972	89.72%
OATP1B3 inhibitior	+	0.9273	92.73%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.4832	48.32%
P-glycoprotein inhibitior	-	0.5359	53.59%
P-glycoprotein substrate	-	0.6909	69.09%
CYP3A4 substrate	+	0.7158	71.58%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8853	88.53%
CYP3A4 inhibition	-	0.9013	90.13%
CYP2C9 inhibition	-	0.9158	91.58%
CYP2C19 inhibition	-	0.9084	90.84%
CYP2D6 inhibition	-	0.9256	92.56%
CYP1A2 inhibition	-	0.8918	89.18%
CYP2C8 inhibition	+	0.5069	50.69%
CYP inhibitory promiscuity	-	0.9396	93.96%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6268	62.68%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9359	93.59%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6759	67.59%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.9025	90.25%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.7658	76.58%
Acute Oral Toxicity (c)	I	0.6455	64.55%
Estrogen receptor binding	+	0.7281	72.81%
Androgen receptor binding	+	0.7710	77.10%
Thyroid receptor binding	+	0.5160	51.60%
Glucocorticoid receptor binding	+	0.6116	61.16%
Aromatase binding	+	0.7037	70.37%
PPAR gamma	+	0.6366	63.66%
Honey bee toxicity	-	0.7156	71.56%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9678	96.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.98%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.91%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.72%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.09%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.57%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.29%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.94%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.05%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.08%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.97%	95.89%
CHEMBL5028	O14672	ADAM10	84.16%	97.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.02%	82.69%
CHEMBL226	P30542	Adenosine A1 receptor	83.64%	95.93%
CHEMBL1977	P11473	Vitamin D receptor	83.24%	99.43%
CHEMBL237	P41145	Kappa opioid receptor	82.41%	98.10%
CHEMBL1937	Q92769	Histone deacetylase 2	81.95%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.86%	97.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.62%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	81.56%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.16%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.77%	97.36%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.20%	91.24%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 162962973
• LOTUS: LTS0114312
• wikiData: Q105297176