(3S)-3-hydroxy-3-methyl-5-oxo-5-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]oxyoxan-2-yl]methoxy]pentanoic acid

Details

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Internal ID 76f07014-a9e2-4452-a052-ec23a2d2a630
Taxonomy Lipids and lipid-like molecules > Saccharolipids
IUPAC Name (3S)-3-hydroxy-3-methyl-5-oxo-5-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]oxyoxan-2-yl]methoxy]pentanoic acid
SMILES (Canonical) CC(CCC1=CC=C(C=C1)O)OC2C(C(C(C(O2)COC(=O)CC(C)(CC(=O)O)O)O)O)O
SMILES (Isomeric) C[C@H](CCC1=CC=C(C=C1)O)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)C[C@](C)(CC(=O)O)O)O)O)O
InChI InChI=1S/C22H32O11/c1-12(3-4-13-5-7-14(23)8-6-13)32-21-20(29)19(28)18(27)15(33-21)11-31-17(26)10-22(2,30)9-16(24)25/h5-8,12,15,18-21,23,27-30H,3-4,9-11H2,1-2H3,(H,24,25)/t12-,15-,18-,19+,20-,21+,22+/m1/s1
InChI Key SBAYJWHOFRCVDL-LBQWKFMXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C22H32O11
Molecular Weight 472.50 g/mol
Exact Mass 472.19446183 g/mol
Topological Polar Surface Area (TPSA) 183.00 Ų
XlogP -0.60
Atomic LogP (AlogP) -0.30
H-Bond Acceptor 10
H-Bond Donor 6
Rotatable Bonds 11

Synonyms

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SCHEMBL20136121

2D Structure

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2D Structure of (3S)-3-hydroxy-3-methyl-5-oxo-5-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]oxyoxan-2-yl]methoxy]pentanoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5466 54.66%
Caco-2 - 0.8220 82.20%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.8523 85.23%
OATP2B1 inhibitior - 0.8613 86.13%
OATP1B1 inhibitior + 0.8410 84.10%
OATP1B3 inhibitior + 0.9014 90.14%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7792 77.92%
BSEP inhibitior - 0.6360 63.60%
P-glycoprotein inhibitior - 0.6554 65.54%
P-glycoprotein substrate - 0.5982 59.82%
CYP3A4 substrate + 0.6476 64.76%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8811 88.11%
CYP3A4 inhibition - 0.7753 77.53%
CYP2C9 inhibition - 0.8092 80.92%
CYP2C19 inhibition - 0.8915 89.15%
CYP2D6 inhibition - 0.9294 92.94%
CYP1A2 inhibition - 0.8481 84.81%
CYP2C8 inhibition - 0.5623 56.23%
CYP inhibitory promiscuity - 0.9425 94.25%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9100 91.00%
Carcinogenicity (trinary) Non-required 0.7131 71.31%
Eye corrosion - 0.9917 99.17%
Eye irritation - 0.9370 93.70%
Skin irritation - 0.7608 76.08%
Skin corrosion - 0.9393 93.93%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3770 37.70%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.6893 68.93%
skin sensitisation - 0.8927 89.27%
Respiratory toxicity + 0.5111 51.11%
Reproductive toxicity + 0.6222 62.22%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity - 0.8886 88.86%
Acute Oral Toxicity (c) III 0.6608 66.08%
Estrogen receptor binding + 0.6872 68.72%
Androgen receptor binding - 0.5381 53.81%
Thyroid receptor binding + 0.5482 54.82%
Glucocorticoid receptor binding + 0.7326 73.26%
Aromatase binding + 0.6242 62.42%
PPAR gamma + 0.5229 52.29%
Honey bee toxicity - 0.7958 79.58%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.7000 70.00%
Fish aquatic toxicity + 0.9547 95.47%

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
CHEMBL2581 P07339 Cathepsin D 98.15% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.86% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.34% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.04% 91.11%
CHEMBL3401 O75469 Pregnane X receptor 94.87% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 93.76% 99.17%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 90.85% 94.62%
CHEMBL3437 Q16853 Amine oxidase, copper containing 90.65% 94.00%
CHEMBL2179 P04062 Beta-glucocerebrosidase 90.43% 85.31%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.80% 85.14%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 89.36% 95.89%
CHEMBL5939 Q9NZ08 Endoplasmic reticulum aminopeptidase 1 88.53% 100.00%
CHEMBL4040 P28482 MAP kinase ERK2 86.91% 83.82%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.71% 86.33%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 84.17% 85.00%
CHEMBL2535 P11166 Glucose transporter 84.16% 98.75%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.97% 93.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.50% 95.89%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.85% 100.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 81.75% 95.56%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.46% 95.50%
CHEMBL2514 O95665 Neurotensin receptor 2 81.04% 100.00%

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.
Betula pendula subsp. mandshurica

Cross-Links

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PubChem 46889079
LOTUS LTS0158996
wikiData Q105249287