methyl (1R,2R,3S,4S,5R,9S,10S,13R,14R)-2,3-dihydroxy-14-(hydroxymethyl)-5,9-dimethyl-14-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate

Details

• Internal ID: f3fbdee5-881a-47ac-90e6-cbf7394a0418
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: methyl (1R,2R,3S,4S,5R,9S,10S,13R,14R)-2,3-dihydroxy-14-(hydroxymethyl)-5,9-dimethyl-14-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• SMILES (Canonical): CC12CCCC(C1C(C(C34C2CCC(C3)C(C4)(CO)OC5C(C(C(C(O5)CO)O)O)O)O)O)(C)C(=O)OC
• SMILES (Isomeric): C[C@@]12CCC[C@@]([C@H]1[C@@H]([C@@H]([C@]34[C@H]2CC[C@H](C3)[C@](C4)(CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)(C)C(=O)OC
• InChI: InChI=1S/C27H44O11/c1-24-7-4-8-25(2,23(35)36-3)20(24)19(33)21(34)26-9-13(5-6-15(24)26)27(11-26,12-29)38-22-18(32)17(31)16(30)14(10-28)37-22/h13-22,28-34H,4-12H2,1-3H3/t13-,14-,15+,16-,17+,18-,19+,20+,21+,22+,24+,25-,26-,27+/m1/s1
• InChI Key: JVEVLHMSSSKCCH-AUHLAWAESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₁₁
• Molecular Weight: 544.60 g/mol
• Exact Mass: 544.28836222 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.94
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5121	51.21%
Caco-2	-	0.8404	84.04%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6917	69.17%
OATP2B1 inhibitior	-	0.5811	58.11%
OATP1B1 inhibitior	+	0.8494	84.94%
OATP1B3 inhibitior	+	0.9167	91.67%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9167	91.67%
P-glycoprotein inhibitior	-	0.5439	54.39%
P-glycoprotein substrate	-	0.6399	63.99%
CYP3A4 substrate	+	0.6957	69.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8513	85.13%
CYP3A4 inhibition	-	0.9525	95.25%
CYP2C9 inhibition	-	0.8551	85.51%
CYP2C19 inhibition	-	0.8035	80.35%
CYP2D6 inhibition	-	0.9618	96.18%
CYP1A2 inhibition	-	0.8491	84.91%
CYP2C8 inhibition	-	0.5616	56.16%
CYP inhibitory promiscuity	-	0.9589	95.89%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7371	73.71%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9402	94.02%
Skin irritation	-	0.7273	72.73%
Skin corrosion	-	0.9535	95.35%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6588	65.88%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7598	75.98%
skin sensitisation	-	0.9354	93.54%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8666	86.66%
Acute Oral Toxicity (c)	I	0.4210	42.10%
Estrogen receptor binding	+	0.5992	59.92%
Androgen receptor binding	+	0.6758	67.58%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5434	54.34%
Aromatase binding	+	0.7244	72.44%
PPAR gamma	+	0.5360	53.60%
Honey bee toxicity	-	0.7754	77.54%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.7923	79.23%

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	98.52%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.64%	96.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	91.72%	95.83%
CHEMBL4072	P07858	Cathepsin B	91.55%	93.67%
CHEMBL5255	O00206	Toll-like receptor 4	89.86%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.49%	97.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.73%	95.50%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.02%	96.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.58%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.56%	96.77%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.45%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.84%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.01%	94.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.84%	91.24%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.75%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.49%	96.21%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.27%	96.00%
CHEMBL2581	P07339	Cathepsin D	81.61%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.14%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.97%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	80.62%	91.19%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.05%	97.50%

Plants that contains it

• Ipomoea nil

Cross-Links

• PubChem: 44179028
• LOTUS: LTS0042502
• wikiData: Q105135649