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(1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-6a-[(Z)-4-(4-hydroxyphenyl)-2-oxobut-3-enyl]-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 f19b8c28-157d-4099-ac85-e3a9bd17fe8b
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)-4-(4-hydroxyphenyl)-2-oxobut-3-enyl]-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)
SMILES (Isomeric)
InChI InChI=1S/C39H54O5/c1-24-15-20-38(34(43)44)21-22-39(23-28(41)12-9-26-7-10-27(40)11-8-26)29(33(38)25(24)2)13-14-31-36(5)18-17-32(42)35(3,4)30(36)16-19-37(31,39)6/h7-13,24-25,30-33,40,42H,14-23H2,1-6H3,(H,43,44)/b12-9-/t24-,25+,30+,31-,32+,33+,36+,37-,38+,39+/m1/s1
InChI Key NOTLGMDYQMIWNO-RZNKELFPSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C39H54O5
Molecular Weight 602.80 g/mol
Exact Mass 602.39712482 g/mol
Topological Polar Surface Area (TPSA) 94.80 Ų
XlogP 8.20
Atomic LogP (AlogP) 8.45
H-Bond Acceptor 4
H-Bond Donor 3
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-6a-[(Z)-4-(4-hydroxyphenyl)-2-oxobut-3-enyl]-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 + 0.9955 99.55%
Caco-2 - 0.8013 80.13%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.8821 88.21%
OATP2B1 inhibitior + 0.5698 56.98%
OATP1B1 inhibitior + 0.8805 88.05%
OATP1B3 inhibitior - 0.4169 41.69%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.9946 99.46%
P-glycoprotein inhibitior + 0.6862 68.62%
P-glycoprotein substrate - 0.5057 50.57%
CYP3A4 substrate + 0.7027 70.27%
CYP2C9 substrate - 0.8054 80.54%
CYP2D6 substrate - 0.8765 87.65%
CYP3A4 inhibition - 0.6135 61.35%
CYP2C9 inhibition - 0.8862 88.62%
CYP2C19 inhibition - 0.8422 84.22%
CYP2D6 inhibition - 0.9382 93.82%
CYP1A2 inhibition - 0.8132 81.32%
CYP2C8 inhibition + 0.7966 79.66%
CYP inhibitory promiscuity - 0.8232 82.32%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9211 92.11%
Carcinogenicity (trinary) Non-required 0.7020 70.20%
Eye corrosion - 0.9958 99.58%
Eye irritation - 0.9375 93.75%
Skin irritation + 0.4910 49.10%
Skin corrosion - 0.9582 95.82%
Ames mutagenesis - 0.7600 76.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6995 69.95%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.5226 52.26%
skin sensitisation - 0.6510 65.10%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity - 0.9105 91.05%
Acute Oral Toxicity (c) III 0.7756 77.56%
Estrogen receptor binding + 0.8045 80.45%
Androgen receptor binding + 0.7888 78.88%
Thyroid receptor binding + 0.5868 58.68%
Glucocorticoid receptor binding + 0.8319 83.19%
Aromatase binding + 0.7060 70.60%
PPAR gamma + 0.7019 70.19%
Honey bee toxicity - 0.7375 73.75%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5400 54.00%
Fish aquatic toxicity + 1.0000 100.00%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL3964 P19174 Phospholipase C-gamma-1 24500 nM
 IC50
 PMID: 19921834

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL221 P23219 Cyclooxygenase-1 96.01% 90.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.73% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.49% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.02% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.54% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.45% 96.09%
CHEMBL3192 Q9BY41 Histone deacetylase 8 89.39% 93.99%
CHEMBL2581 P07339 Cathepsin D 89.03% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.79% 94.45%
CHEMBL206 P03372 Estrogen receptor alpha 87.64% 97.64%
CHEMBL226 P30542 Adenosine A1 receptor 87.59% 95.93%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.04% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.79% 89.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.07% 95.89%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.53% 95.89%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 81.12% 91.71%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.09% 93.00%
CHEMBL340 P08684 Cytochrome P450 3A4 80.74% 91.19%
CHEMBL2514 O95665 Neurotensin receptor 2 80.46% 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.
Uncaria rhynchophylla

Cross-Links

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PubChem 44583699
NPASS NPC475457
ChEMBL CHEMBL506008
LOTUS LTS0074785
wikiData Q105182771