methyl 6-[3-formyl-4-(2-methoxy-2-oxoethyl)-2-methyl-3,4-dihydro-2H-pyran-5-carbonyl]oxy-1-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

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Internal ID 223f4805-63d4-4501-acf9-ed4b64d38021
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
IUPAC Name methyl 6-[3-formyl-4-(2-methoxy-2-oxoethyl)-2-methyl-3,4-dihydro-2H-pyran-5-carbonyl]oxy-1-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
SMILES (Canonical) CC1C(CC2C1C(OC=C2C(=O)OC)O)OC(=O)C3=COC(C(C3CC(=O)OC)C=O)C
SMILES (Isomeric) CC1C(CC2C1C(OC=C2C(=O)OC)O)OC(=O)C3=COC(C(C3CC(=O)OC)C=O)C
InChI InChI=1S/C22H28O10/c1-10-17(5-13-16(20(25)29-4)9-31-22(27)19(10)13)32-21(26)15-8-30-11(2)14(7-23)12(15)6-18(24)28-3/h7-14,17,19,22,27H,5-6H2,1-4H3
InChI Key OGVKQJQFXCWBTO-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H28O10
Molecular Weight 452.50 g/mol
Exact Mass 452.16824709 g/mol
Topological Polar Surface Area (TPSA) 135.00 Ų
XlogP 0.60
Atomic LogP (AlogP) 0.87
H-Bond Acceptor 10
H-Bond Donor 1
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl 6-[3-formyl-4-(2-methoxy-2-oxoethyl)-2-methyl-3,4-dihydro-2H-pyran-5-carbonyl]oxy-1-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 + 0.9595 95.95%
Caco-2 - 0.7339 73.39%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.6807 68.07%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.6920 69.20%
OATP1B3 inhibitior + 0.8741 87.41%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.6794 67.94%
P-glycoprotein inhibitior + 0.6887 68.87%
P-glycoprotein substrate + 0.5266 52.66%
CYP3A4 substrate + 0.6510 65.10%
CYP2C9 substrate + 0.6000 60.00%
CYP2D6 substrate - 0.8749 87.49%
CYP3A4 inhibition - 0.7696 76.96%
CYP2C9 inhibition - 0.8563 85.63%
CYP2C19 inhibition - 0.8928 89.28%
CYP2D6 inhibition - 0.9136 91.36%
CYP1A2 inhibition - 0.8523 85.23%
CYP2C8 inhibition + 0.6858 68.58%
CYP inhibitory promiscuity - 0.6691 66.91%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9813 98.13%
Carcinogenicity (trinary) Non-required 0.4854 48.54%
Eye corrosion - 0.9839 98.39%
Eye irritation - 0.9415 94.15%
Skin irritation - 0.6316 63.16%
Skin corrosion - 0.9427 94.27%
Ames mutagenesis + 0.5546 55.46%
Human Ether-a-go-go-Related Gene inhibition - 0.6976 69.76%
Micronuclear - 0.5600 56.00%
Hepatotoxicity - 0.5608 56.08%
skin sensitisation - 0.8343 83.43%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity - 0.6819 68.19%
Acute Oral Toxicity (c) I 0.3653 36.53%
Estrogen receptor binding + 0.8112 81.12%
Androgen receptor binding + 0.5958 59.58%
Thyroid receptor binding - 0.5325 53.25%
Glucocorticoid receptor binding + 0.5829 58.29%
Aromatase binding - 0.6217 62.17%
PPAR gamma - 0.4852 48.52%
Honey bee toxicity - 0.8323 83.23%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.8666 86.66%

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 97.38% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.33% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.44% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 85.14% 94.73%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 84.65% 86.92%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.60% 97.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.31% 99.17%
CHEMBL5028 O14672 ADAM10 83.08% 97.50%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 82.46% 96.00%
CHEMBL4208 P20618 Proteasome component C5 81.91% 90.00%
CHEMBL340 P08684 Cytochrome P450 3A4 81.65% 91.19%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 80.48% 97.21%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.12% 94.33%

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.
Scaevola floribunda

Cross-Links

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PubChem 85191263
LOTUS LTS0226078
wikiData Q105191890