(4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-6a-[[(1R,2S)-3-[[(4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-4a-carboxy-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-6a-yl]methoxycarbonyl]-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxymethyl]-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Details

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Internal ID 1e39899b-b2e7-4d45-b76e-859cae0b54d8
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-6a-[[(1R,2S)-3-[[(4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-4a-carboxy-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-6a-yl]methoxycarbonyl]-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxymethyl]-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
SMILES (Canonical) CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)COC(=O)C6C(C7=CC(=C(C=C7C=C6C(=O)OCC89CCC1(CCC(CC1C8=CCC1C9(CCC2C1(CCC(C2(C)C)O)C)C)(C)C)C(=O)O)O)O)C1=CC(=C(C=C1)O)O)C(=O)O)C
SMILES (Isomeric) C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)COC(=O)[C@H]6[C@@H](C7=CC(=C(C=C7C=C6C(=O)OC[C@@]89CC[C@]1(CCC(C[C@H]1C8=CC[C@H]1[C@]9(CC[C@@H]2[C@@]1(CC[C@@H](C2(C)C)O)C)C)(C)C)C(=O)O)O)O)C1=CC(=C(C=C1)O)O)C)(C)C)O
InChI InChI=1S/C78H106O14/c1-67(2)27-29-75(65(87)88)31-33-77(47(49(75)39-67)14-17-57-71(9)23-21-59(83)69(5,6)55(71)19-25-73(57,77)11)41-91-63(85)46-35-44-37-53(81)54(82)38-45(44)61(43-13-16-51(79)52(80)36-43)62(46)64(86)92-42-78-34-32-76(66(89)90)30-28-68(3,4)40-50(76)48(78)15-18-58-72(10)24-22-60(84)70(7,8)56(72)20-26-74(58,78)12/h13-16,35-38,49-50,55-62,79-84H,17-34,39-42H2,1-12H3,(H,87,88)(H,89,90)/t49-,50-,55-,56-,57+,58+,59-,60-,61+,62+,71-,72-,73+,74+,75-,76-,77-,78-/m0/s1
InChI Key QOVKXRBEKCDPME-KMLVZOICSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C78H106O14
Molecular Weight 1267.70 g/mol
Exact Mass 1266.75825805 g/mol
Topological Polar Surface Area (TPSA) 249.00 Ų
XlogP 15.30
Atomic LogP (AlogP) 15.20
H-Bond Acceptor 12
H-Bond Donor 8
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-6a-[[(1R,2S)-3-[[(4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-4a-carboxy-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-6a-yl]methoxycarbonyl]-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxymethyl]-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9871 98.71%
Caco-2 - 0.8553 85.53%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.9286 92.86%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8235 82.35%
OATP1B3 inhibitior + 0.8066 80.66%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.8026 80.26%
BSEP inhibitior + 0.9862 98.62%
P-glycoprotein inhibitior + 0.7470 74.70%
P-glycoprotein substrate + 0.5698 56.98%
CYP3A4 substrate + 0.7308 73.08%
CYP2C9 substrate - 0.8004 80.04%
CYP2D6 substrate - 0.8730 87.30%
CYP3A4 inhibition - 0.7921 79.21%
CYP2C9 inhibition - 0.7161 71.61%
CYP2C19 inhibition - 0.7210 72.10%
CYP2D6 inhibition - 0.9152 91.52%
CYP1A2 inhibition - 0.5772 57.72%
CYP2C8 inhibition + 0.8147 81.47%
CYP inhibitory promiscuity - 0.8832 88.32%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9000 90.00%
Carcinogenicity (trinary) Non-required 0.6601 66.01%
Eye corrosion - 0.9925 99.25%
Eye irritation - 0.8978 89.78%
Skin irritation - 0.7346 73.46%
Skin corrosion - 0.9573 95.73%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6639 66.39%
Micronuclear - 0.7100 71.00%
Hepatotoxicity - 0.6875 68.75%
skin sensitisation - 0.8581 85.81%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity - 0.8854 88.54%
Acute Oral Toxicity (c) III 0.5491 54.91%
Estrogen receptor binding + 0.6437 64.37%
Androgen receptor binding + 0.7784 77.84%
Thyroid receptor binding + 0.6822 68.22%
Glucocorticoid receptor binding + 0.7828 78.28%
Aromatase binding + 0.6777 67.77%
PPAR gamma + 0.8127 81.27%
Honey bee toxicity - 0.6963 69.63%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5605 56.05%
Fish aquatic toxicity + 1.0000 100.00%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.17% 91.11%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 98.82% 95.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.95% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 97.63% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.89% 94.45%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 92.58% 99.15%
CHEMBL2581 P07339 Cathepsin D 91.40% 98.95%
CHEMBL226 P30542 Adenosine A1 receptor 91.33% 95.93%
CHEMBL221 P23219 Cyclooxygenase-1 90.30% 90.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.04% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.79% 95.56%
CHEMBL5028 O14672 ADAM10 84.79% 97.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.72% 100.00%
CHEMBL5255 O00206 Toll-like receptor 4 83.15% 92.50%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 82.19% 82.69%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.65% 86.33%
CHEMBL340 P08684 Cytochrome P450 3A4 81.12% 91.19%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 80.74% 96.38%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 80.36% 90.71%

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.
Rhoiptelea chiliantha

Cross-Links

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PubChem 15275972
LOTUS LTS0103047
wikiData Q105225146