3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-17-(1-hydroxy-5-methylhex-4-enyl)-8,14-dimethyl-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde

Details

Top
Internal ID 5cfe7a77-99f1-4f39-b0fc-268b1c671583
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
IUPAC Name 3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-17-(1-hydroxy-5-methylhex-4-enyl)-8,14-dimethyl-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde
SMILES (Canonical) CC(=CCCC(C1CCC2(C1CCC3C2(CCC4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C=O)C)C)O)C
SMILES (Isomeric) CC(=CCCC(C1CCC2(C1CCC3C2(CCC4C3(CCC(C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C=O)C)C)O)C
InChI InChI=1S/C39H64O13/c1-20(2)6-5-7-25(43)23-12-14-37(3)24(23)8-9-28-38(37,4)13-10-21-16-22(11-15-39(21,28)19-42)49-36-34(32(47)30(45)27(18-41)51-36)52-35-33(48)31(46)29(44)26(17-40)50-35/h6,19,21-36,40-41,43-48H,5,7-18H2,1-4H3/t21?,22?,23?,24?,25?,26-,27-,28?,29-,30-,31+,32+,33-,34-,35+,36-,37?,38?,39?/m1/s1
InChI Key GVBDPCPLRGCHQH-QLRGAEDESA-N
Popularity 2 references in papers

Physical and Chemical Properties

Top
Molecular Formula C39H64O13
Molecular Weight 740.90 g/mol
Exact Mass 740.43469209 g/mol
Topological Polar Surface Area (TPSA) 216.00 Ų
XlogP 3.00
Atomic LogP (AlogP) 1.33
H-Bond Acceptor 13
H-Bond Donor 8
Rotatable Bonds 11

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of 3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-17-(1-hydroxy-5-methylhex-4-enyl)-8,14-dimethyl-1,2,3,4,5,6,7,9,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7719 77.19%
Caco-2 - 0.8841 88.41%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.8134 81.34%
OATP2B1 inhibitior - 0.7336 73.36%
OATP1B1 inhibitior + 0.8646 86.46%
OATP1B3 inhibitior - 0.2428 24.28%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.6776 67.76%
BSEP inhibitior + 0.7029 70.29%
P-glycoprotein inhibitior + 0.7192 71.92%
P-glycoprotein substrate - 0.5917 59.17%
CYP3A4 substrate + 0.7281 72.81%
CYP2C9 substrate - 0.8022 80.22%
CYP2D6 substrate - 0.8296 82.96%
CYP3A4 inhibition - 0.9469 94.69%
CYP2C9 inhibition - 0.8637 86.37%
CYP2C19 inhibition - 0.9118 91.18%
CYP2D6 inhibition - 0.9391 93.91%
CYP1A2 inhibition - 0.9069 90.69%
CYP2C8 inhibition + 0.5673 56.73%
CYP inhibitory promiscuity - 0.9514 95.14%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6516 65.16%
Eye corrosion - 0.9913 99.13%
Eye irritation - 0.9166 91.66%
Skin irritation - 0.5512 55.12%
Skin corrosion - 0.9480 94.80%
Ames mutagenesis - 0.7600 76.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7873 78.73%
Micronuclear - 0.8800 88.00%
Hepatotoxicity - 0.7039 70.39%
skin sensitisation - 0.9013 90.13%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity - 0.5875 58.75%
Nephrotoxicity + 0.7399 73.99%
Acute Oral Toxicity (c) I 0.4409 44.09%
Estrogen receptor binding + 0.8122 81.22%
Androgen receptor binding + 0.7744 77.44%
Thyroid receptor binding - 0.5975 59.75%
Glucocorticoid receptor binding + 0.6132 61.32%
Aromatase binding + 0.6465 64.65%
PPAR gamma + 0.6803 68.03%
Honey bee toxicity - 0.5996 59.96%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 0.9413 94.13%

Targets

Top

Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.39% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.00% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.00% 96.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 93.74% 96.61%
CHEMBL233 P35372 Mu opioid receptor 93.70% 97.93%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 93.29% 92.86%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.89% 97.09%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 92.04% 96.38%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 90.10% 91.24%
CHEMBL2094135 Q96BI3 Gamma-secretase 90.10% 98.05%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 89.26% 97.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.94% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.67% 100.00%
CHEMBL1937 Q92769 Histone deacetylase 2 88.56% 94.75%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.32% 85.14%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 88.26% 95.71%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 87.75% 94.23%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 87.37% 95.50%
CHEMBL253 P34972 Cannabinoid CB2 receptor 86.82% 97.25%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 86.20% 95.58%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 85.28% 94.62%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 84.91% 93.10%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.83% 95.89%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 84.22% 94.33%
CHEMBL3892 Q99500 Sphingosine 1-phosphate receptor Edg-3 82.70% 97.29%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 82.53% 100.00%
CHEMBL279 P35968 Vascular endothelial growth factor receptor 2 81.65% 95.52%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 81.61% 96.90%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.46% 99.17%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.77% 100.00%
CHEMBL2413 P32246 C-C chemokine receptor type 1 80.42% 89.50%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.20% 92.62%

Plants that contains it

Top
Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Gymnema sylvestre
Gynostemma pentaphyllum

Cross-Links

Top
PubChem 5317936
NPASS NPC18838
LOTUS LTS0018764
wikiData Q105107418