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methyl (1S,4aS,6S,7R,7aS)-1-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-5-(3-hydroxybenzoyl)oxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-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

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Internal ID 0051ef91-a5d3-4873-84aa-7a7e5ae2e17e
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aS,6S,7R,7aS)-1-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-5-(3-hydroxybenzoyl)oxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
SMILES (Canonical) CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)OC(=O)C4=CC(=CC=C4)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)OC(=O)C4=CC(=CC=C4)O)O)O)O
InChI InChI=1S/C24H30O12/c1-10-15(27)7-13-14(22(31)32-2)9-33-23(17(10)13)36-24-19(29)18(28)20(16(8-25)34-24)35-21(30)11-4-3-5-12(26)6-11/h3-6,9-10,13,15-20,23-29H,7-8H2,1-2H3/t10-,13+,15-,16+,17+,18+,19+,20+,23-,24-/m0/s1
InChI Key WHKMGTMLDBTICD-HNYWUSPDSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C24H30O12
Molecular Weight 510.50 g/mol
Exact Mass 510.17372639 g/mol
Topological Polar Surface Area (TPSA) 181.00 Ų
XlogP -0.10
Atomic LogP (AlogP) -0.58
H-Bond Acceptor 12
H-Bond Donor 5
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,4aS,6S,7R,7aS)-1-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-5-(3-hydroxybenzoyl)oxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8838 88.38%
Caco-2 - 0.8677 86.77%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.6555 65.55%
OATP2B1 inhibitior - 0.8608 86.08%
OATP1B1 inhibitior - 0.3643 36.43%
OATP1B3 inhibitior + 0.9339 93.39%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.9107 91.07%
P-glycoprotein inhibitior - 0.6446 64.46%
P-glycoprotein substrate + 0.5828 58.28%
CYP3A4 substrate + 0.6913 69.13%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8591 85.91%
CYP3A4 inhibition - 0.7295 72.95%
CYP2C9 inhibition - 0.8039 80.39%
CYP2C19 inhibition - 0.7975 79.75%
CYP2D6 inhibition - 0.8480 84.80%
CYP1A2 inhibition - 0.7344 73.44%
CYP2C8 inhibition + 0.7042 70.42%
CYP inhibitory promiscuity - 0.7703 77.03%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6317 63.17%
Eye corrosion - 0.9895 98.95%
Eye irritation - 0.9335 93.35%
Skin irritation - 0.7286 72.86%
Skin corrosion - 0.9459 94.59%
Ames mutagenesis + 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4051 40.51%
Micronuclear - 0.5500 55.00%
Hepatotoxicity - 0.5726 57.26%
skin sensitisation - 0.8263 82.63%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity - 0.7622 76.22%
Acute Oral Toxicity (c) III 0.4611 46.11%
Estrogen receptor binding + 0.7942 79.42%
Androgen receptor binding + 0.5330 53.30%
Thyroid receptor binding - 0.5198 51.98%
Glucocorticoid receptor binding + 0.6385 63.85%
Aromatase binding + 0.5214 52.14%
PPAR gamma + 0.5991 59.91%
Honey bee toxicity - 0.7983 79.83%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.7200 72.00%
Fish aquatic toxicity + 0.8814 88.14%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.16% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.40% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.10% 97.09%
CHEMBL2581 P07339 Cathepsin D 94.71% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 94.51% 94.73%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.44% 85.14%
CHEMBL3060 Q9Y345 Glycine transporter 2 92.53% 99.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.01% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.91% 86.33%
CHEMBL4208 P20618 Proteasome component C5 90.98% 90.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 90.87% 95.83%
CHEMBL2535 P11166 Glucose transporter 85.43% 98.75%
CHEMBL340 P08684 Cytochrome P450 3A4 84.90% 91.19%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 84.53% 96.95%
CHEMBL1951 P21397 Monoamine oxidase A 84.08% 91.49%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.14% 95.89%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.37% 91.07%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.32% 99.23%

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.
Gentiana verna

Cross-Links

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PubChem 162913340
LOTUS LTS0165653
wikiData Q105305378