(5R,9R,10R,12R,13S,14R,17S)-12-hydroxy-17-[(2R,3S)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one

Details

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Internal ID 8100c507-3873-48bc-8f71-86816e1a0f76
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (5R,9R,10R,12R,13S,14R,17S)-12-hydroxy-17-[(2R,3S)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
SMILES (Canonical) CC(C1CCC2(C1(C(CC3C2=CCC4C3(CCC(=O)C4(C)C)C)O)C)C)C(C(=O)C=C(C)C)O
SMILES (Isomeric) C[C@H]([C@@H]1CC[C@]2([C@]1([C@@H](C[C@H]3C2=CC[C@@H]4[C@@]3(CCC(=O)C4(C)C)C)O)C)C)[C@@H](C(=O)C=C(C)C)O
InChI InChI=1S/C30H46O4/c1-17(2)15-22(31)26(34)18(3)19-11-14-29(7)20-9-10-23-27(4,5)24(32)12-13-28(23,6)21(20)16-25(33)30(19,29)8/h9,15,18-19,21,23,25-26,33-34H,10-14,16H2,1-8H3/t18-,19+,21+,23+,25-,26+,28-,29-,30-/m1/s1
InChI Key TYZVNQRTVOXOJE-BQUAPPCPSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C30H46O4
Molecular Weight 470.70 g/mol
Exact Mass 470.33960994 g/mol
Topological Polar Surface Area (TPSA) 74.60 Ų
XlogP 5.60
Atomic LogP (AlogP) 5.66
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (5R,9R,10R,12R,13S,14R,17S)-12-hydroxy-17-[(2R,3S)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9934 99.34%
Caco-2 - 0.5356 53.56%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.8327 83.27%
OATP2B1 inhibitior - 0.8614 86.14%
OATP1B1 inhibitior + 0.8789 87.89%
OATP1B3 inhibitior + 0.9340 93.40%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior + 0.6500 65.00%
BSEP inhibitior + 0.9359 93.59%
P-glycoprotein inhibitior - 0.4423 44.23%
P-glycoprotein substrate - 0.5331 53.31%
CYP3A4 substrate + 0.6452 64.52%
CYP2C9 substrate - 0.7411 74.11%
CYP2D6 substrate - 0.8673 86.73%
CYP3A4 inhibition - 0.8586 85.86%
CYP2C9 inhibition - 0.8781 87.81%
CYP2C19 inhibition - 0.9397 93.97%
CYP2D6 inhibition - 0.9443 94.43%
CYP1A2 inhibition - 0.8944 89.44%
CYP2C8 inhibition - 0.5877 58.77%
CYP inhibitory promiscuity - 0.9030 90.30%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6217 62.17%
Eye corrosion - 0.9945 99.45%
Eye irritation - 0.9445 94.45%
Skin irritation + 0.7336 73.36%
Skin corrosion - 0.9449 94.49%
Ames mutagenesis - 0.7200 72.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5000 50.00%
Micronuclear - 0.8200 82.00%
Hepatotoxicity - 0.5000 50.00%
skin sensitisation - 0.6612 66.12%
Respiratory toxicity + 0.7889 78.89%
Reproductive toxicity + 0.9889 98.89%
Mitochondrial toxicity + 1.0000 100.00%
Nephrotoxicity - 0.7995 79.95%
Acute Oral Toxicity (c) III 0.6045 60.45%
Estrogen receptor binding + 0.7820 78.20%
Androgen receptor binding + 0.7861 78.61%
Thyroid receptor binding + 0.6759 67.59%
Glucocorticoid receptor binding + 0.8248 82.48%
Aromatase binding + 0.7403 74.03%
PPAR gamma + 0.5966 59.66%
Honey bee toxicity - 0.8116 81.16%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity - 0.7400 74.00%
Fish aquatic toxicity + 0.9934 99.34%

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 96.29% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.82% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.41% 94.45%
CHEMBL4224 P49759 Dual specificty protein kinase CLK1 90.40% 85.30%
CHEMBL2581 P07339 Cathepsin D 90.38% 98.95%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 88.12% 90.71%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.98% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.63% 100.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.67% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.47% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.35% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 84.97% 91.19%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.91% 93.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.56% 89.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.55% 91.07%

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.
Melia azedarach

Cross-Links

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PubChem 46210321
LOTUS LTS0017156
wikiData Q105267834