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3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic 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 1a8689ff-5cfe-4e6d-a108-7e1d78ad4da1
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,3,4,5,6,8,8a,10,11,12,14,14b-dodecahydropicene-2-carboxylic acid
SMILES (Canonical) CC1(C(CCC2(C1CC=C3C2=CCC4(C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C)OC(=O)C=CC6=CC=C(C=C6)O)C
SMILES (Isomeric) C[C@]12CC[C@@](C[C@H]1[C@@]3(CC=C4C(=CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OC(=O)/C=C/C6=CC=C(C=C6)O)C)[C@]3(CC2)C)C)(C)C(=O)O
InChI InChI=1S/C39H52O5/c1-34(2)29-14-13-28-27(37(29,5)18-17-31(34)44-32(41)15-10-25-8-11-26(40)12-9-25)16-19-39(7)30-24-36(4,33(42)43)21-20-35(30,3)22-23-38(28,39)6/h8-13,15-16,29-31,40H,14,17-24H2,1-7H3,(H,42,43)/b15-10+/t29-,30+,31-,35+,36+,37+,38+,39-/m0/s1
InChI Key NOTQCQMXZCILJE-WYGBHMDXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C39H52O5
Molecular Weight 600.80 g/mol
Exact Mass 600.38147475 g/mol
Topological Polar Surface Area (TPSA) 83.80 Ų
XlogP 9.20
Atomic LogP (AlogP) 9.12
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 4

Synonyms

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(2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydropicene-2-carboxylic acid
CHEBI:65663
DTXSID501105694
Q27134145
(2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,3,4,5,6,8,8a,10,11,12,14,14b-dodecahydropicene-2-carboxylic acid
(3beta,13alpha,14beta,20alpha)-3-[[(2E)-3-(4-Hydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-13-methyl-26-noroleana-7,9(11)-dien-29-oic acid
1038596-65-4

2D Structure

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2D Structure of 3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9948 99.48%
Caco-2 - 0.7765 77.65%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.9118 91.18%
OATP2B1 inhibitior - 0.7149 71.49%
OATP1B1 inhibitior + 0.8327 83.27%
OATP1B3 inhibitior - 0.6488 64.88%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.7071 70.71%
BSEP inhibitior + 0.9964 99.64%
P-glycoprotein inhibitior + 0.8265 82.65%
P-glycoprotein substrate - 0.5073 50.73%
CYP3A4 substrate + 0.6899 68.99%
CYP2C9 substrate - 0.8038 80.38%
CYP2D6 substrate - 0.8877 88.77%
CYP3A4 inhibition - 0.7360 73.60%
CYP2C9 inhibition - 0.7710 77.10%
CYP2C19 inhibition - 0.7538 75.38%
CYP2D6 inhibition - 0.9317 93.17%
CYP1A2 inhibition + 0.5713 57.13%
CYP2C8 inhibition + 0.8607 86.07%
CYP inhibitory promiscuity - 0.8119 81.19%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9255 92.55%
Carcinogenicity (trinary) Non-required 0.6449 64.49%
Eye corrosion - 0.9950 99.50%
Eye irritation - 0.9282 92.82%
Skin irritation - 0.5654 56.54%
Skin corrosion - 0.9641 96.41%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8010 80.10%
Micronuclear - 0.6600 66.00%
Hepatotoxicity - 0.6791 67.91%
skin sensitisation - 0.6590 65.90%
Respiratory toxicity + 0.5111 51.11%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity + 0.6233 62.33%
Acute Oral Toxicity (c) III 0.7095 70.95%
Estrogen receptor binding + 0.7633 76.33%
Androgen receptor binding + 0.7561 75.61%
Thyroid receptor binding + 0.6442 64.42%
Glucocorticoid receptor binding + 0.8216 82.16%
Aromatase binding + 0.7197 71.97%
PPAR gamma + 0.7064 70.64%
Honey bee toxicity - 0.7437 74.37%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5055 50.55%
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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.68% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.10% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.79% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.13% 96.09%
CHEMBL206 P03372 Estrogen receptor alpha 90.19% 97.64%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.17% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.71% 86.33%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 88.47% 94.97%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 87.78% 91.71%
CHEMBL2581 P07339 Cathepsin D 85.47% 98.95%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 84.91% 94.62%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.58% 95.89%
CHEMBL241 Q14432 Phosphodiesterase 3A 84.49% 92.94%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 83.80% 89.62%
CHEMBL242 Q92731 Estrogen receptor beta 83.26% 98.35%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 82.01% 94.23%
CHEMBL340 P08684 Cytochrome P450 3A4 81.92% 91.19%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 81.43% 94.78%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.38% 100.00%
CHEMBL4208 P20618 Proteasome component C5 81.20% 90.00%
CHEMBL245 P20309 Muscarinic acetylcholine receptor M3 80.16% 97.53%

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.
Lagenaria siceraria

Cross-Links

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PubChem 24850702
LOTUS LTS0054942
wikiData Q27134145