[(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (2E,4E)-5-[(1R,6R)-1-hydroxy-2,2,6-trimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexyl]-3-methylpenta-2,4-dienoate

Details

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Internal ID 98475a73-64fe-42fa-9051-92869acc6691
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name [(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (2E,4E)-5-[(1R,6R)-1-hydroxy-2,2,6-trimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexyl]-3-methylpenta-2,4-dienoate
SMILES (Canonical) CC(=CC(=O)OC1CC(C2C1C=COC2OC3C(C(C(C(O3)CO)O)O)O)(C)O)C=CC4(C(CCCC4(C)OC5C(C(C(C(O5)CO)O)O)O)(C)C)O
SMILES (Isomeric) C/C(=C\C(=O)O[C@@H]1C[C@]([C@@H]2[C@H]1C=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)(C)O)/C=C/[C@@]4([C@](CCCC4(C)C)(C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
InChI InChI=1S/C36H56O17/c1-17(7-11-36(47)33(2,3)9-6-10-35(36,5)53-32-29(45)27(43)25(41)21(16-38)51-32)13-22(39)49-19-14-34(4,46)23-18(19)8-12-48-30(23)52-31-28(44)26(42)24(40)20(15-37)50-31/h7-8,11-13,18-21,23-32,37-38,40-47H,6,9-10,14-16H2,1-5H3/b11-7+,17-13+/t18-,19+,20+,21+,23+,24+,25+,26-,27-,28+,29+,30-,31-,32-,34-,35+,36+/m0/s1
InChI Key OEVHHOBYWIPRBU-DGUBVJKLSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C36H56O17
Molecular Weight 760.80 g/mol
Exact Mass 760.35175031 g/mol
Topological Polar Surface Area (TPSA) 275.00 Ų
XlogP -0.90
Atomic LogP (AlogP) -2.01
H-Bond Acceptor 17
H-Bond Donor 10
Rotatable Bonds 10

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,4aR,5R,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] (2E,4E)-5-[(1R,6R)-1-hydroxy-2,2,6-trimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexyl]-3-methylpenta-2,4-dienoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7626 76.26%
Caco-2 - 0.8778 87.78%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.7767 77.67%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8367 83.67%
OATP1B3 inhibitior - 0.2385 23.85%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7276 72.76%
BSEP inhibitior + 0.8357 83.57%
P-glycoprotein inhibitior + 0.7062 70.62%
P-glycoprotein substrate - 0.5092 50.92%
CYP3A4 substrate + 0.7303 73.03%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8935 89.35%
CYP3A4 inhibition - 0.9522 95.22%
CYP2C9 inhibition - 0.8504 85.04%
CYP2C19 inhibition - 0.9128 91.28%
CYP2D6 inhibition - 0.9337 93.37%
CYP1A2 inhibition - 0.8980 89.80%
CYP2C8 inhibition + 0.5751 57.51%
CYP inhibitory promiscuity - 0.9424 94.24%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6593 65.93%
Eye corrosion - 0.9910 99.10%
Eye irritation - 0.9124 91.24%
Skin irritation - 0.5842 58.42%
Skin corrosion - 0.9414 94.14%
Ames mutagenesis - 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7096 70.96%
Micronuclear - 0.8700 87.00%
Hepatotoxicity - 0.7351 73.51%
skin sensitisation - 0.8866 88.66%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity - 0.5750 57.50%
Nephrotoxicity - 0.8810 88.10%
Acute Oral Toxicity (c) III 0.4408 44.08%
Estrogen receptor binding + 0.8019 80.19%
Androgen receptor binding + 0.6913 69.13%
Thyroid receptor binding + 0.5213 52.13%
Glucocorticoid receptor binding + 0.6383 63.83%
Aromatase binding + 0.6065 60.65%
PPAR gamma + 0.7320 73.20%
Honey bee toxicity - 0.6019 60.19%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.8698 86.98%

Targets

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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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.71% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.17% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.48% 86.33%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 91.64% 91.24%
CHEMBL1937 Q92769 Histone deacetylase 2 90.63% 94.75%
CHEMBL221 P23219 Cyclooxygenase-1 88.18% 90.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.84% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.29% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 86.02% 94.73%
CHEMBL5255 O00206 Toll-like receptor 4 85.24% 92.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.50% 100.00%
CHEMBL226 P30542 Adenosine A1 receptor 83.88% 95.93%
CHEMBL340 P08684 Cytochrome P450 3A4 83.64% 91.19%
CHEMBL253 P34972 Cannabinoid CB2 receptor 83.29% 97.25%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 83.24% 97.50%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.16% 91.07%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 83.01% 95.83%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 82.76% 95.50%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.68% 100.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 82.23% 96.00%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 81.18% 98.75%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.48% 95.89%

Plants that contains it

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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.
Rehmannia glutinosa

Cross-Links

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PubChem 71449969
NPASS NPC219804
LOTUS LTS0164115
wikiData Q105190585