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[(2R,3R,4R,5R)-2,3,4,5,6-Pentahydroxyhexyl] (2E,4S,5S,6E,8S,9S,10E,12S,13R,14S,16S,18S)-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethyl-13-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyicosa-2,6,10-trienoate

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 3587a89b-a192-4de2-afb3-22ce0434f2c8
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids
IUPAC Name [(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl] (2E,4S,5S,6E,8S,9S,10E,12S,13R,14S,16S,18S)-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethyl-13-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyicosa-2,6,10-trienoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C41H74O15/c1-11-20(2)12-21(3)13-26(8)39(56-41-38(52)37(51)36(50)31(18-43)55-41)27(9)15-24(6)32(46)22(4)14-23(5)33(47)25(7)16-28(10)40(53)54-19-30(45)35(49)34(48)29(44)17-42/h14-16,20-22,25-27,29-39,41-52H,11-13,17-19H2,1-10H3/b23-14+,24-15+,28-16+/t20-,21-,22-,25-,26-,27-,29+,30+,31+,32-,33+,34+,35+,36+,37-,38-,39+,41-/m0/s1
InChI Key VIWWSCLCWIDLRT-RFEPXNHGSA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C41H74O15
Molecular Weight 807.00 g/mol
Exact Mass 806.50277165 g/mol
Topological Polar Surface Area (TPSA) 267.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 0.72
H-Bond Acceptor 15
H-Bond Donor 11
Rotatable Bonds 24

Synonyms

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TMC-151 C
240807-75-4
[(2R,3R,4R,5R)-2,3,4,5,6-Pentahydroxyhexyl] (2E,4S,5S,6E,8S,9S,10E,12S,13R,14S,16S,18S)-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethyl-13-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyicosa-2,6,10-trienoate
TMC-151C
orb2279412
CHEMBL3344123
CHEBI:220335
AKOS040735242

2D Structure

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2D Structure of [(2R,3R,4R,5R)-2,3,4,5,6-Pentahydroxyhexyl] (2E,4S,5S,6E,8S,9S,10E,12S,13R,14S,16S,18S)-5,9-dihydroxy-2,4,6,8,10,12,14,16,18-nonamethyl-13-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyicosa-2,6,10-trienoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5877 58.77%
Caco-2 - 0.8735 87.35%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.7616 76.16%
OATP2B1 inhibitior - 0.8616 86.16%
OATP1B1 inhibitior + 0.8426 84.26%
OATP1B3 inhibitior + 0.9172 91.72%
MATE1 inhibitior - 0.8812 88.12%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.8553 85.53%
P-glycoprotein inhibitior + 0.6924 69.24%
P-glycoprotein substrate - 0.5153 51.53%
CYP3A4 substrate + 0.6713 67.13%
CYP2C9 substrate - 0.8028 80.28%
CYP2D6 substrate - 0.8858 88.58%
CYP3A4 inhibition - 0.8447 84.47%
CYP2C9 inhibition - 0.8938 89.38%
CYP2C19 inhibition - 0.7845 78.45%
CYP2D6 inhibition - 0.9126 91.26%
CYP1A2 inhibition - 0.8570 85.70%
CYP2C8 inhibition + 0.4873 48.73%
CYP inhibitory promiscuity - 0.9347 93.47%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.7515 75.15%
Eye corrosion - 0.9912 99.12%
Eye irritation - 0.9088 90.88%
Skin irritation - 0.7752 77.52%
Skin corrosion - 0.9624 96.24%
Ames mutagenesis - 0.6237 62.37%
Human Ether-a-go-go-Related Gene inhibition + 0.6445 64.45%
Micronuclear - 0.8600 86.00%
Hepatotoxicity - 0.5875 58.75%
skin sensitisation - 0.8742 87.42%
Respiratory toxicity - 0.5111 51.11%
Reproductive toxicity - 0.5556 55.56%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity + 0.5721 57.21%
Acute Oral Toxicity (c) III 0.6343 63.43%
Estrogen receptor binding + 0.8286 82.86%
Androgen receptor binding + 0.5717 57.17%
Thyroid receptor binding + 0.5335 53.35%
Glucocorticoid receptor binding + 0.7051 70.51%
Aromatase binding + 0.6091 60.91%
PPAR gamma + 0.7358 73.58%
Honey bee toxicity - 0.7187 71.87%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.7500 75.00%
Fish aquatic toxicity + 0.8331 83.31%

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 97.77% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.88% 97.25%
CHEMBL2581 P07339 Cathepsin D 95.47% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.63% 91.11%
CHEMBL3060 Q9Y345 Glycine transporter 2 93.48% 99.17%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 92.52% 96.47%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 92.22% 85.14%
CHEMBL3401 O75469 Pregnane X receptor 91.99% 94.73%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 91.19% 96.95%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 90.10% 98.75%
CHEMBL221 P23219 Cyclooxygenase-1 88.41% 90.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.35% 89.00%
CHEMBL226 P30542 Adenosine A1 receptor 86.25% 95.93%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 86.19% 97.21%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.06% 99.23%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 84.46% 96.00%
CHEMBL2360 P00492 Hypoxanthine-guanine phosphoribosyltransferase 83.97% 87.38%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.68% 93.56%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.77% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.66% 97.09%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.56% 97.14%

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.
There are no matching plants.

Cross-Links

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PubChem 10581222
LOTUS LTS0197736
wikiData Q77569007