(2R,3R,4R,5R,6S)-2-[(E)-5-[(1S,4S,4aR,5R,8aR)-4-hydroxy-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoxy]-6-methyloxane-3,4,5-triol

Details

• Internal ID: 7c63b94f-b6eb-4050-9058-f2ffbe7fae3e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (2R,3R,4R,5R,6S)-2-[(E)-5-[(1S,4S,4aR,5R,8aR)-4-hydroxy-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoxy]-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OCC=C(C)CCC2C(=C)CC(C3C2(CCCC3(C)COC4C(C(C(C(O4)CO)O)O)O)C)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC/C=C(\C)/CC[C@H]2C(=C)C[C@@H]([C@@H]3[C@@]2(CCC[C@@]3(C)CO[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)C)O)O)O)O
• InChI: InChI=1S/C32H54O12/c1-16(9-12-41-29-26(39)24(37)22(35)18(3)43-29)7-8-19-17(2)13-20(34)28-31(4,10-6-11-32(19,28)5)15-42-30-27(40)25(38)23(36)21(14-33)44-30/h9,18-30,33-40H,2,6-8,10-15H2,1,3-5H3/b16-9+/t18-,19-,20-,21+,22-,23-,24+,25-,26+,27+,28-,29+,30+,31-,32+/m0/s1
• InChI Key: PUHVSLQDLDYLBX-CHBHBLRQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₅₄O₁₂
• Molecular Weight: 630.80 g/mol
• Exact Mass: 630.36152715 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.12
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4639	46.39%
Caco-2	-	0.8708	87.08%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6467	64.67%
OATP2B1 inhibitior	-	0.8613	86.13%
OATP1B1 inhibitior	+	0.7580	75.80%
OATP1B3 inhibitior	+	0.8091	80.91%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.5317	53.17%
P-glycoprotein inhibitior	+	0.6396	63.96%
P-glycoprotein substrate	-	0.5553	55.53%
CYP3A4 substrate	+	0.6790	67.90%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9070	90.70%
CYP2C9 inhibition	-	0.8998	89.98%
CYP2C19 inhibition	-	0.8681	86.81%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.8796	87.96%
CYP2C8 inhibition	+	0.6427	64.27%
CYP inhibitory promiscuity	-	0.9644	96.44%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6855	68.55%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9301	93.01%
Skin irritation	-	0.5844	58.44%
Skin corrosion	-	0.9486	94.86%
Ames mutagenesis	-	0.5824	58.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8409	84.09%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.8040	80.40%
skin sensitisation	-	0.9000	90.00%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.9054	90.54%
Acute Oral Toxicity (c)	III	0.4855	48.55%
Estrogen receptor binding	+	0.7453	74.53%
Androgen receptor binding	+	0.6865	68.65%
Thyroid receptor binding	-	0.5611	56.11%
Glucocorticoid receptor binding	-	0.4717	47.17%
Aromatase binding	+	0.6586	65.86%
PPAR gamma	+	0.6265	62.65%
Honey bee toxicity	-	0.7118	71.18%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9350	93.50%

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	99.05%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.66%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	94.61%	91.49%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.37%	96.61%
CHEMBL2581	P07339	Cathepsin D	92.02%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.54%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.12%	86.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.55%	95.50%
CHEMBL233	P35372	Mu opioid receptor	89.53%	97.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.17%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	88.24%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.24%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.84%	89.00%
CHEMBL1977	P11473	Vitamin D receptor	87.54%	99.43%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.26%	97.36%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.09%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.80%	91.24%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.70%	95.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.66%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	83.44%	94.73%
CHEMBL3589	P55263	Adenosine kinase	80.02%	98.05%

Plants that contains it

• Mitraria coccinea

Cross-Links

• PubChem: 162931638
• LOTUS: LTS0020732
• wikiData: Q105215101