(2S,3R,4S,5R,6R)-2-[[(1S,1aR,4R,4aS,7R,7aS,7bS)-1,4,7-trimethyl-1-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy]-6-methyloxane-3,4,5-triol

Details

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Internal ID c9c149e1-6315-4bc1-8d97-89cfd90b6772
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
IUPAC Name (2S,3R,4S,5R,6R)-2-[[(1S,1aR,4R,4aS,7R,7aS,7bS)-1,4,7-trimethyl-1-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy]-6-methyloxane-3,4,5-triol
SMILES (Canonical) CC1CCC2C1C3C(C3(C)COC4C(C(C(C(O4)CO)O)O)O)CCC2(C)OC5C(C(C(C(O5)C)O)O)O
SMILES (Isomeric) C[C@@H]1CC[C@H]2[C@@H]1[C@H]3[C@H]([C@]3(C)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)CC[C@@]2(C)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)C)O)O)O
InChI InChI=1S/C27H46O11/c1-11-5-6-13-16(11)17-14(7-8-27(13,4)38-25-23(34)20(31)18(29)12(2)36-25)26(17,3)10-35-24-22(33)21(32)19(30)15(9-28)37-24/h11-25,28-34H,5-10H2,1-4H3/t11-,12-,13+,14-,15-,16-,17-,18+,19-,20+,21+,22-,23-,24-,25+,26+,27-/m1/s1
InChI Key QMZPCWAILBCLFF-JGVVKRRYSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C27H46O11
Molecular Weight 546.60 g/mol
Exact Mass 546.30401228 g/mol
Topological Polar Surface Area (TPSA) 179.00 Ų
XlogP -0.20
Atomic LogP (AlogP) -0.89
H-Bond Acceptor 11
H-Bond Donor 7
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3R,4S,5R,6R)-2-[[(1S,1aR,4R,4aS,7R,7aS,7bS)-1,4,7-trimethyl-1-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy]-6-methyloxane-3,4,5-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6188 61.88%
Caco-2 - 0.8592 85.92%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.6018 60.18%
OATP2B1 inhibitior - 0.7255 72.55%
OATP1B1 inhibitior + 0.8785 87.85%
OATP1B3 inhibitior + 0.9287 92.87%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.5750 57.50%
BSEP inhibitior - 0.9278 92.78%
P-glycoprotein inhibitior - 0.5482 54.82%
P-glycoprotein substrate - 0.7702 77.02%
CYP3A4 substrate + 0.6792 67.92%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8203 82.03%
CYP3A4 inhibition - 0.9674 96.74%
CYP2C9 inhibition - 0.8419 84.19%
CYP2C19 inhibition - 0.8250 82.50%
CYP2D6 inhibition - 0.9549 95.49%
CYP1A2 inhibition - 0.8701 87.01%
CYP2C8 inhibition + 0.5163 51.63%
CYP inhibitory promiscuity - 0.9431 94.31%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6917 69.17%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9272 92.72%
Skin irritation - 0.7271 72.71%
Skin corrosion - 0.9510 95.10%
Ames mutagenesis - 0.7307 73.07%
Human Ether-a-go-go-Related Gene inhibition + 0.6684 66.84%
Micronuclear - 0.8200 82.00%
Hepatotoxicity - 0.7372 73.72%
skin sensitisation - 0.9300 93.00%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.6778 67.78%
Mitochondrial toxicity - 0.5625 56.25%
Nephrotoxicity - 0.8690 86.90%
Acute Oral Toxicity (c) I 0.6262 62.62%
Estrogen receptor binding + 0.6023 60.23%
Androgen receptor binding + 0.5736 57.36%
Thyroid receptor binding - 0.4907 49.07%
Glucocorticoid receptor binding - 0.4779 47.79%
Aromatase binding + 0.6467 64.67%
PPAR gamma + 0.6104 61.04%
Honey bee toxicity - 0.6627 66.27%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity + 0.8141 81.41%

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 97.49% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.31% 91.11%
CHEMBL218 P21554 Cannabinoid CB1 receptor 94.97% 96.61%
CHEMBL226 P30542 Adenosine A1 receptor 94.50% 95.93%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.81% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.62% 97.25%
CHEMBL237 P41145 Kappa opioid receptor 88.91% 98.10%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.53% 86.33%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 87.07% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.86% 100.00%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 86.67% 96.38%
CHEMBL2243 O00519 Anandamide amidohydrolase 85.17% 97.53%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 84.51% 95.83%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.30% 95.89%
CHEMBL1937 Q92769 Histone deacetylase 2 83.62% 94.75%
CHEMBL233 P35372 Mu opioid receptor 83.28% 97.93%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 82.93% 96.77%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 82.28% 95.50%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 81.97% 86.92%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.84% 92.94%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 80.56% 96.21%

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.
Calendula officinalis

Cross-Links

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PubChem 10951715
NPASS NPC193585
LOTUS LTS0242391
wikiData Q105224276