(4aS,6aS,6bR,12aR)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid

Details

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Internal ID ba2eed28-8048-47ca-9785-0be09e0d8c60
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (4aS,6aS,6bR,12aR)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
SMILES (Canonical) CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(=O)C5(C)C)C)C)C2C1)C)C(=O)O)C
SMILES (Isomeric) C[C@]12CCC(=O)C(C1CC[C@@]3(C2CC=C4[C@]3(CC[C@@]5(C4CC(CC5)(C)C)C(=O)O)C)C)(C)C
InChI InChI=1S/C30H46O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-22H,9-18H2,1-7H3,(H,32,33)/t20?,21?,22?,27-,28+,29+,30-/m0/s1
InChI Key FMIMFCRXYXVFTA-YUVMXPMLSA-N
Popularity 6 references in papers

Physical and Chemical Properties

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Molecular Formula C30H46O3
Molecular Weight 454.70 g/mol
Exact Mass 454.34469533 g/mol
Topological Polar Surface Area (TPSA) 54.40 Ų
XlogP 7.20
Atomic LogP (AlogP) 7.44
H-Bond Acceptor 2
H-Bond Donor 1
Rotatable Bonds 1

Synonyms

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(4aS,6aS,6bR,12aR)-2,2,6a,6b,9,9,12a-Heptamethyl-10-oxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid
(4aS,6aS,6bR,12aR)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
Oleanolic acid, 3-oxo
SCHEMBL12313105
FMIMFCRXYXVFTA-YUVMXPMLSA-N
BDBM50165430
(4aS,6aS,6bR,12aR)-2,2,6a,6b,9,9,12a-Heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4-a-carboxylic acid
(4aS,6aS,6bR,8aR,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

2D Structure

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2D Structure of (4aS,6aS,6bR,12aR)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-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 + 0.9961 99.61%
Caco-2 + 0.5180 51.80%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability + 0.5429 54.29%
Subcellular localzation Mitochondria 0.9052 90.52%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7853 78.53%
OATP1B3 inhibitior + 0.8126 81.26%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior + 0.6500 65.00%
BSEP inhibitior + 0.9427 94.27%
P-glycoprotein inhibitior - 0.6469 64.69%
P-glycoprotein substrate - 0.8552 85.52%
CYP3A4 substrate + 0.6063 60.63%
CYP2C9 substrate - 0.6106 61.06%
CYP2D6 substrate - 0.8683 86.83%
CYP3A4 inhibition - 0.8315 83.15%
CYP2C9 inhibition - 0.8584 85.84%
CYP2C19 inhibition - 0.8273 82.73%
CYP2D6 inhibition - 0.9514 95.14%
CYP1A2 inhibition - 0.8772 87.72%
CYP2C8 inhibition - 0.6206 62.06%
CYP inhibitory promiscuity - 0.9345 93.45%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5882 58.82%
Eye corrosion - 0.9942 99.42%
Eye irritation - 0.9025 90.25%
Skin irritation + 0.6222 62.22%
Skin corrosion - 0.9601 96.01%
Ames mutagenesis - 0.8400 84.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5098 50.98%
Micronuclear - 0.7600 76.00%
Hepatotoxicity - 0.8125 81.25%
skin sensitisation + 0.5846 58.46%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity - 0.5786 57.86%
Acute Oral Toxicity (c) III 0.7802 78.02%
Estrogen receptor binding + 0.7976 79.76%
Androgen receptor binding + 0.6788 67.88%
Thyroid receptor binding + 0.6934 69.34%
Glucocorticoid receptor binding + 0.8415 84.15%
Aromatase binding + 0.7115 71.15%
PPAR gamma + 0.7302 73.02%
Honey bee toxicity - 0.9039 90.39%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity + 1.0000 100.00%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL4081 P13726 Coagulation factor III 0.221 nM
IC50
via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.00% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.04% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.41% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.14% 99.23%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.08% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.88% 96.09%
CHEMBL2581 P07339 Cathepsin D 83.41% 98.95%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 83.35% 95.17%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 82.40% 93.00%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 82.02% 93.03%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.49% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.15% 82.69%

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 macrophylla
Uncaria rhynchophylla
Uncaria sinensis

Cross-Links

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PubChem 470665
NPASS NPC49818