PlantaeDB Logo
Login Sign-up

methyl (1R,4aR,7S,7aR)-5'-oxo-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4'-[(1R)-1-[(E)-3-[4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxyethyl]spiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

Top
Internal ID e90d05da-12ac-465c-8566-dbafc1e4e983
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1R,4aR,7S,7aR)-5'-oxo-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4'-[(1R)-1-[(E)-3-[4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxyethyl]spiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
SMILES (Canonical) CC(C1=CC2(C=CC3C2C(OC=C3C(=O)OC)OC4C(C(C(C(O4)CO)O)O)O)OC1=O)OC(=O)C=CC5=CC=C(C=C5)OC6C(C(C(C(O6)CO)O)O)O
SMILES (Isomeric) C[C@H](C1=C[C@]2(C=C[C@@H]3[C@H]2[C@H](OC=C3C(=O)OC)O[C@@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O)OC1=O)OC(=O)/C=C/C5=CC=C(C=C5)O[C@@H]6[C@H]([C@@H]([C@H]([C@@H](O6)CO)O)O)O
InChI InChI=1S/C36H42O19/c1-15(50-23(39)8-5-16-3-6-17(7-4-16)51-34-29(44)27(42)25(40)21(12-37)52-34)19-11-36(55-32(19)47)10-9-18-20(31(46)48-2)14-49-33(24(18)36)54-35-30(45)28(43)26(41)22(13-38)53-35/h3-11,14-15,18,21-22,24-30,33-35,37-38,40-45H,12-13H2,1-2H3/b8-5+/t15-,18+,21+,22+,24+,25+,26+,27-,28-,29+,30+,33-,34+,35-,36+/m1/s1
InChI Key AFYIWKNGSIYXCQ-KAYJCYQMSA-N
Popularity 3 references in papers

Physical and Chemical Properties

Top
Molecular Formula C36H42O19
Molecular Weight 778.70 g/mol
Exact Mass 778.23202911 g/mol
Topological Polar Surface Area (TPSA) 287.00 Ų
XlogP -1.30
Atomic LogP (AlogP) -2.94
H-Bond Acceptor 19
H-Bond Donor 8
Rotatable Bonds 11

Synonyms

Top
80396-57-2

2D Structure

Top
2D Structure of methyl (1R,4aR,7S,7aR)-5'-oxo-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4'-[(1R)-1-[(E)-3-[4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoyl]oxyethyl]spiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6614 66.14%
Caco-2 - 0.8747 87.47%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.6866 68.66%
OATP2B1 inhibitior - 0.7148 71.48%
OATP1B1 inhibitior + 0.8080 80.80%
OATP1B3 inhibitior + 0.9513 95.13%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.9541 95.41%
P-glycoprotein inhibitior + 0.7109 71.09%
P-glycoprotein substrate + 0.5671 56.71%
CYP3A4 substrate + 0.7117 71.17%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8799 87.99%
CYP3A4 inhibition - 0.8790 87.90%
CYP2C9 inhibition - 0.8297 82.97%
CYP2C19 inhibition - 0.7677 76.77%
CYP2D6 inhibition - 0.9090 90.90%
CYP1A2 inhibition - 0.8920 89.20%
CYP2C8 inhibition + 0.7283 72.83%
CYP inhibitory promiscuity - 0.6266 62.66%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5373 53.73%
Eye corrosion - 0.9880 98.80%
Eye irritation - 0.9100 91.00%
Skin irritation - 0.7770 77.70%
Skin corrosion - 0.9398 93.98%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8203 82.03%
Micronuclear + 0.5433 54.33%
Hepatotoxicity - 0.7457 74.57%
skin sensitisation - 0.7944 79.44%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity + 0.7334 73.34%
Acute Oral Toxicity (c) III 0.5337 53.37%
Estrogen receptor binding + 0.7882 78.82%
Androgen receptor binding + 0.6878 68.78%
Thyroid receptor binding + 0.5655 56.55%
Glucocorticoid receptor binding + 0.7260 72.60%
Aromatase binding + 0.5478 54.78%
PPAR gamma + 0.7262 72.62%
Honey bee toxicity - 0.6800 68.00%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6000 60.00%
Fish aquatic toxicity + 0.8386 83.86%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.01% 91.11%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 97.23% 96.00%
CHEMBL2581 P07339 Cathepsin D 95.63% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.22% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.05% 96.09%
CHEMBL221 P23219 Cyclooxygenase-1 94.93% 90.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.78% 89.00%
CHEMBL3401 O75469 Pregnane X receptor 91.29% 94.73%
CHEMBL4208 P20618 Proteasome component C5 91.12% 90.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.05% 95.56%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 90.13% 91.07%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.69% 97.09%
CHEMBL226 P30542 Adenosine A1 receptor 87.10% 95.93%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.69% 95.89%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.39% 99.17%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.35% 85.14%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 86.03% 89.67%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 85.09% 92.88%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.22% 94.45%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 82.19% 95.83%
CHEMBL5028 O14672 ADAM10 81.23% 97.50%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.23% 95.50%

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.
Allamanda schottii
Plumeria rubra

Cross-Links

Top
PubChem 133561887
LOTUS LTS0169112
wikiData Q104911634