[(2S,3S,4aR,5R,8aS)-3-[(2R,3S,4R,5R,6S)-4-acetyloxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,1,4a,6-tetramethyl-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: ba5599d6-8acc-4be7-b898-3ead8719d6f3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2S,3S,4aR,5R,8aS)-3-[(2R,3S,4R,5R,6S)-4-acetyloxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,1,4a,6-tetramethyl-2,3,4,5,8,8a-hexahydronaphthalen-2-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(CC2(C(C1(C)C)CC=C(C2CCC(=CCO)C)C)C)OC3C(C(C(C(O3)C)O)OC(=O)C)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1[C@H](C[C@]2([C@@H](C1(C)C)CC=C([C@H]2CC/C(=C/CO)/C)C)C)O[C@@H]3[C@H]([C@@H]([C@@H]([C@@H](O3)C)O)OC(=O)C)O
• InChI: InChI=1S/C33H52O9/c1-10-19(3)30(38)42-29-24(41-31-27(37)28(40-22(6)35)26(36)21(5)39-31)17-33(9)23(13-11-18(2)15-16-34)20(4)12-14-25(33)32(29,7)8/h10,12,15,21,23-29,31,34,36-37H,11,13-14,16-17H2,1-9H3/b18-15+,19-10-/t21-,23+,24-,25+,26+,27-,28+,29+,31+,33+/m0/s1
• InChI Key: OUPWATZPEVLKGS-IDNLWVQASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₂O₉
• Molecular Weight: 592.80 g/mol
• Exact Mass: 592.36113323 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.39
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8323	83.23%
Caco-2	-	0.7931	79.31%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8425	84.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8219	82.19%
OATP1B3 inhibitior	+	0.8291	82.91%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9102	91.02%
P-glycoprotein inhibitior	+	0.7856	78.56%
P-glycoprotein substrate	-	0.5138	51.38%
CYP3A4 substrate	+	0.7032	70.32%
CYP2C9 substrate	-	0.7976	79.76%
CYP2D6 substrate	-	0.8995	89.95%
CYP3A4 inhibition	-	0.7823	78.23%
CYP2C9 inhibition	-	0.8396	83.96%
CYP2C19 inhibition	-	0.8923	89.23%
CYP2D6 inhibition	-	0.9358	93.58%
CYP1A2 inhibition	-	0.7117	71.17%
CYP2C8 inhibition	+	0.5634	56.34%
CYP inhibitory promiscuity	-	0.8384	83.84%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6983	69.83%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9251	92.51%
Skin irritation	-	0.5463	54.63%
Skin corrosion	-	0.9532	95.32%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4032	40.32%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6494	64.94%
skin sensitisation	-	0.8833	88.33%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6688	66.88%
Acute Oral Toxicity (c)	III	0.7779	77.79%
Estrogen receptor binding	+	0.7113	71.13%
Androgen receptor binding	+	0.5751	57.51%
Thyroid receptor binding	-	0.5438	54.38%
Glucocorticoid receptor binding	+	0.6998	69.98%
Aromatase binding	+	0.6818	68.18%
PPAR gamma	+	0.6720	67.20%
Honey bee toxicity	-	0.6913	69.13%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9722	97.22%

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	98.55%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.53%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.55%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	92.28%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.34%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.93%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	90.69%	94.73%
CHEMBL2581	P07339	Cathepsin D	88.70%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.34%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.17%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.02%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.92%	93.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.02%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.59%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.49%	89.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.78%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.36%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.76%	97.36%

Plants that contains it

• Gymnosperma glutinosum

Cross-Links

• PubChem: 162853052
• LOTUS: LTS0078265
• wikiData: Q105200352