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

Details

• Internal ID: 596e9d72-d049-4eba-9d07-bdb262c3bbbd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2S,3S,4aR,5R,8aS)-3-[(2R,3S,4S,5S,6S)-5-acetyloxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-5-[(4R)-4,5-dihydroxy-3-methylidenepentyl]-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(=C)C(CO)O)C)C)OC3C(C(C(C(O3)C)OC(=O)C)O)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]2CCC(=C)[C@H](CO)O)C)C)O[C@@H]3[C@H]([C@@H]([C@@H]([C@@H](O3)C)OC(=O)C)O)O
• InChI: InChI=1S/C33H52O10/c1-10-17(2)30(39)43-29-24(42-31-27(38)26(37)28(20(5)40-31)41-21(6)35)15-33(9)22(13-11-19(4)23(36)16-34)18(3)12-14-25(33)32(29,7)8/h10,12,20,22-29,31,34,36-38H,4,11,13-16H2,1-3,5-9H3/b17-10-/t20-,22+,23-,24-,25+,26-,27-,28+,29+,31+,33+/m0/s1
• InChI Key: UHUVXQZKXHSANE-SUEMHOALSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₂O₁₀
• Molecular Weight: 608.80 g/mol
• Exact Mass: 608.35604785 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.36
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8952	89.52%
Caco-2	-	0.8231	82.31%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8617	86.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8380	83.80%
OATP1B3 inhibitior	+	0.8024	80.24%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5568	55.68%
BSEP inhibitior	+	0.7923	79.23%
P-glycoprotein inhibitior	+	0.7311	73.11%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7008	70.08%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.8973	89.73%
CYP3A4 inhibition	+	0.5503	55.03%
CYP2C9 inhibition	-	0.7429	74.29%
CYP2C19 inhibition	-	0.8074	80.74%
CYP2D6 inhibition	-	0.9482	94.82%
CYP1A2 inhibition	-	0.6726	67.26%
CYP2C8 inhibition	+	0.5621	56.21%
CYP inhibitory promiscuity	-	0.9560	95.60%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7186	71.86%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9224	92.24%
Skin irritation	-	0.5138	51.38%
Skin corrosion	-	0.9462	94.62%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7282	72.82%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6622	66.22%
skin sensitisation	-	0.8766	87.66%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6682	66.82%
Acute Oral Toxicity (c)	III	0.7086	70.86%
Estrogen receptor binding	+	0.7677	76.77%
Androgen receptor binding	+	0.6027	60.27%
Thyroid receptor binding	-	0.5174	51.74%
Glucocorticoid receptor binding	+	0.7609	76.09%
Aromatase binding	+	0.7257	72.57%
PPAR gamma	+	0.7115	71.15%
Honey bee toxicity	-	0.6544	65.44%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9872	98.72%

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	98.74%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.64%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.10%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	91.62%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.60%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.83%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.70%	97.25%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.19%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.13%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.42%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.17%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	88.47%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.30%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.94%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.94%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.64%	97.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.05%	91.24%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.58%	96.47%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.31%	91.07%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.60%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.40%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.59%	91.19%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	80.40%	80.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.19%	93.00%

Plants that contains it

• Gymnosperma glutinosum

Cross-Links

• PubChem: 163106168
• LOTUS: LTS0141118
• wikiData: Q105273105