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(1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-6a-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1,2,6b,9,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

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 fa8a7277-9cde-4ae5-a974-b763e1ec4ddf
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-6a-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1,2,6b,9,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
SMILES (Canonical) CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1C)COC(=O)C=CC6=CC=C(C=C6)O)C(=O)O
SMILES (Isomeric) C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)COC(=O)/C=C\C6=CC=C(C=C6)O)C(=O)O
InChI InChI=1S/C39H54O6/c1-24-15-20-38(34(43)44)21-22-39(23-45-32(42)14-9-26-7-10-27(40)11-8-26)28(33(38)25(24)2)12-13-30-36(5)18-17-31(41)35(3,4)29(36)16-19-37(30,39)6/h7-12,14,24-25,29-31,33,40-41H,13,15-23H2,1-6H3,(H,43,44)/b14-9-/t24-,25+,29+,30-,31+,33+,36+,37-,38+,39+/m1/s1
InChI Key RZHJGXXCTIXCRI-NLOWRNJMSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C39H54O6
Molecular Weight 618.80 g/mol
Exact Mass 618.39203944 g/mol
Topological Polar Surface Area (TPSA) 104.00 Ų
XlogP 8.20
Atomic LogP (AlogP) 8.03
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 5

Synonyms

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NSC640464
CHEMBL4579133
(1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-6a-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1,2,6b,9,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
3-Hydroxy-27-((3-(4-hydroxyphenyl)acryloyl)oxy)urs-12-en-28-oic acid

2D Structure

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2D Structure of (1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-6a-[[(Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1,2,6b,9,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-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 + 0.9957 99.57%
Caco-2 - 0.8016 80.16%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.9339 93.39%
OATP2B1 inhibitior - 0.5670 56.70%
OATP1B1 inhibitior + 0.8682 86.82%
OATP1B3 inhibitior - 0.2958 29.58%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.7183 71.83%
BSEP inhibitior + 0.9896 98.96%
P-glycoprotein inhibitior + 0.7441 74.41%
P-glycoprotein substrate - 0.5102 51.02%
CYP3A4 substrate + 0.7162 71.62%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8772 87.72%
CYP3A4 inhibition - 0.6788 67.88%
CYP2C9 inhibition - 0.7220 72.20%
CYP2C19 inhibition - 0.7677 76.77%
CYP2D6 inhibition - 0.9150 91.50%
CYP1A2 inhibition - 0.5589 55.89%
CYP2C8 inhibition + 0.8358 83.58%
CYP inhibitory promiscuity - 0.7441 74.41%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.6870 68.70%
Eye corrosion - 0.9951 99.51%
Eye irritation - 0.9310 93.10%
Skin irritation - 0.6231 62.31%
Skin corrosion - 0.9701 97.01%
Ames mutagenesis - 0.7500 75.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6802 68.02%
Micronuclear - 0.7300 73.00%
Hepatotoxicity - 0.5750 57.50%
skin sensitisation - 0.8054 80.54%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity - 0.9361 93.61%
Acute Oral Toxicity (c) III 0.7024 70.24%
Estrogen receptor binding + 0.7979 79.79%
Androgen receptor binding + 0.7955 79.55%
Thyroid receptor binding + 0.5494 54.94%
Glucocorticoid receptor binding + 0.8367 83.67%
Aromatase binding + 0.7354 73.54%
PPAR gamma + 0.7325 73.25%
Honey bee toxicity - 0.7039 70.39%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.5445 54.45%
Fish aquatic toxicity + 1.0000 100.00%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL203 P00533 Epidermal growth factor receptor erbB1 56.48 nM
 IC50
 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.02% 86.33%
CHEMBL221 P23219 Cyclooxygenase-1 95.87% 90.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.65% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.96% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.46% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.37% 96.09%
CHEMBL2581 P07339 Cathepsin D 90.52% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.27% 94.45%
CHEMBL206 P03372 Estrogen receptor alpha 85.46% 97.64%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.72% 95.89%
CHEMBL4227 P25090 Lipoxin A4 receptor 84.38% 100.00%
CHEMBL1937 Q92769 Histone deacetylase 2 84.27% 94.75%
CHEMBL3192 Q9BY41 Histone deacetylase 8 84.04% 93.99%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.78% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.05% 95.89%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.24% 93.00%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 80.36% 91.71%

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.
Uncaria rhynchophylla
Viburnum jucundum

Cross-Links

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PubChem 6477980
LOTUS LTS0161188
wikiData Q105248390