methyl 7-methyl-6-(7-methyl-1-oxo-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-4-carbonyl)oxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

Top
Internal ID 29820d99-7834-491e-aaf8-08df87028b2e
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl 7-methyl-6-(7-methyl-1-oxo-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-4-carbonyl)oxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
SMILES (Canonical) CC1CCC2C1C(=O)OCC2C(=O)OC3CC4C(C3C)C(OC=C4C(=O)OC)OC5C(C(C(C(O5)CO)O)O)O
SMILES (Isomeric) CC1CCC2C1C(=O)OCC2C(=O)OC3CC4C(C3C)C(OC=C4C(=O)OC)OC5C(C(C(C(O5)CO)O)O)O
InChI InChI=1S/C27H38O13/c1-10-4-5-12-14(8-36-25(34)18(10)12)24(33)38-16-6-13-15(23(32)35-3)9-37-26(19(13)11(16)2)40-27-22(31)21(30)20(29)17(7-28)39-27/h9-14,16-22,26-31H,4-8H2,1-3H3
InChI Key BQMYRPGSJXGSKG-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C27H38O13
Molecular Weight 570.60 g/mol
Exact Mass 570.23124126 g/mol
Topological Polar Surface Area (TPSA) 188.00 Ų
XlogP 0.70
Atomic LogP (AlogP) -0.76
H-Bond Acceptor 13
H-Bond Donor 4
Rotatable Bonds 6

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of methyl 7-methyl-6-(7-methyl-1-oxo-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-4-carbonyl)oxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5677 56.77%
Caco-2 - 0.8525 85.25%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.7936 79.36%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.6984 69.84%
OATP1B3 inhibitior + 0.9141 91.41%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior - 0.5639 56.39%
P-glycoprotein inhibitior - 0.4895 48.95%
P-glycoprotein substrate + 0.5982 59.82%
CYP3A4 substrate + 0.7043 70.43%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8889 88.89%
CYP3A4 inhibition - 0.8968 89.68%
CYP2C9 inhibition - 0.9222 92.22%
CYP2C19 inhibition - 0.8844 88.44%
CYP2D6 inhibition - 0.9352 93.52%
CYP1A2 inhibition - 0.8305 83.05%
CYP2C8 inhibition + 0.6340 63.40%
CYP inhibitory promiscuity - 0.9445 94.45%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6995 69.95%
Eye corrosion - 0.9895 98.95%
Eye irritation - 0.9358 93.58%
Skin irritation - 0.6828 68.28%
Skin corrosion - 0.9532 95.32%
Ames mutagenesis - 0.5506 55.06%
Human Ether-a-go-go-Related Gene inhibition - 0.3974 39.74%
Micronuclear - 0.8600 86.00%
Hepatotoxicity - 0.6375 63.75%
skin sensitisation - 0.9223 92.23%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity + 0.5000 50.00%
Acute Oral Toxicity (c) III 0.4279 42.79%
Estrogen receptor binding + 0.8148 81.48%
Androgen receptor binding + 0.6406 64.06%
Thyroid receptor binding - 0.5924 59.24%
Glucocorticoid receptor binding + 0.6363 63.63%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.5788 57.88%
Honey bee toxicity - 0.7230 72.30%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6900 69.00%
Fish aquatic toxicity + 0.9308 93.08%

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 98.20% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.18% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.91% 97.09%
CHEMBL2581 P07339 Cathepsin D 90.17% 98.95%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 90.12% 86.92%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 89.18% 94.80%
CHEMBL5255 O00206 Toll-like receptor 4 88.65% 92.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.95% 89.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 85.85% 96.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.57% 85.14%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 83.46% 95.83%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.33% 100.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 81.13% 94.33%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.87% 86.33%
CHEMBL5028 O14672 ADAM10 80.01% 97.50%

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.
Galium maximowiczii

Cross-Links

Top
PubChem 73113959
LOTUS LTS0089787
wikiData Q104944450