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methyl (1S,4aS,7R,7aS)-1-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4'-[(S)-hydroxy-(4-hydroxy-3-methoxyphenyl)methyl]-5'-oxospiro[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

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Internal ID 94bab097-0dcf-4992-8a16-d61f3c0d4124
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name methyl (1S,4aS,7R,7aS)-1-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4'-[(S)-hydroxy-(4-hydroxy-3-methoxyphenyl)methyl]-5'-oxospiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
SMILES (Canonical) CC(=O)OCC1C(C(C(C(O1)OC2C3C(C=CC34C=C(C(=O)O4)C(C5=CC(=C(C=C5)O)OC)O)C(=CO2)C(=O)OC)O)O)O
SMILES (Isomeric) CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H]3[C@H](C=C[C@@]34C=C(C(=O)O4)[C@H](C5=CC(=C(C=C5)O)OC)O)C(=CO2)C(=O)OC)O)O)O
InChI InChI=1S/C29H32O15/c1-12(30)40-11-19-22(33)23(34)24(35)28(42-19)43-27-20-14(16(10-41-27)25(36)39-3)6-7-29(20)9-15(26(37)44-29)21(32)13-4-5-17(31)18(8-13)38-2/h4-10,14,19-24,27-28,31-35H,11H2,1-3H3/t14-,19-,20-,21+,22-,23+,24-,27+,28+,29-/m1/s1
InChI Key UJGUSKGCTXMCER-JFPLEXQZSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H32O15
Molecular Weight 620.60 g/mol
Exact Mass 620.17412031 g/mol
Topological Polar Surface Area (TPSA) 217.00 Ų
XlogP -0.30
Atomic LogP (AlogP) -0.74
H-Bond Acceptor 15
H-Bond Donor 5
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,4aS,7R,7aS)-1-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4'-[(S)-hydroxy-(4-hydroxy-3-methoxyphenyl)methyl]-5'-oxospiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-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 + 0.8839 88.39%
Caco-2 - 0.8924 89.24%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.6327 63.27%
OATP2B1 inhibitior - 0.5732 57.32%
OATP1B1 inhibitior + 0.7861 78.61%
OATP1B3 inhibitior + 0.9170 91.70%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.8312 83.12%
P-glycoprotein inhibitior + 0.6417 64.17%
P-glycoprotein substrate + 0.5999 59.99%
CYP3A4 substrate + 0.6976 69.76%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8746 87.46%
CYP3A4 inhibition - 0.8995 89.95%
CYP2C9 inhibition - 0.7502 75.02%
CYP2C19 inhibition - 0.7355 73.55%
CYP2D6 inhibition - 0.8897 88.97%
CYP1A2 inhibition - 0.7315 73.15%
CYP2C8 inhibition + 0.7420 74.20%
CYP inhibitory promiscuity - 0.6137 61.37%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6118 61.18%
Eye corrosion - 0.9888 98.88%
Eye irritation - 0.9164 91.64%
Skin irritation - 0.7412 74.12%
Skin corrosion - 0.9362 93.62%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3643 36.43%
Micronuclear + 0.5492 54.92%
Hepatotoxicity - 0.6030 60.30%
skin sensitisation - 0.8160 81.60%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity - 0.6002 60.02%
Acute Oral Toxicity (c) III 0.4456 44.56%
Estrogen receptor binding + 0.8367 83.67%
Androgen receptor binding + 0.6452 64.52%
Thyroid receptor binding + 0.5623 56.23%
Glucocorticoid receptor binding + 0.7510 75.10%
Aromatase binding + 0.5216 52.16%
PPAR gamma + 0.6812 68.12%
Honey bee toxicity - 0.7496 74.96%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity + 0.9657 96.57%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 99.89% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.63% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.98% 96.09%
CHEMBL2581 P07339 Cathepsin D 96.07% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.37% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.95% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.64% 89.00%
CHEMBL4208 P20618 Proteasome component C5 93.58% 90.00%
CHEMBL3401 O75469 Pregnane X receptor 91.00% 94.73%
CHEMBL2535 P11166 Glucose transporter 90.02% 98.75%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 89.66% 96.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.47% 95.56%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.10% 99.17%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 86.18% 97.21%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 85.72% 92.62%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 85.19% 99.15%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.07% 94.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.62% 95.89%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 82.52% 94.80%
CHEMBL5028 O14672 ADAM10 81.59% 97.50%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.85% 95.50%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 80.36% 96.90%

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.
Morinda morindoides

Cross-Links

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PubChem 46864995
LOTUS LTS0195934
wikiData Q105273928