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(2R)-2-[(3S,10S,13R,14R,16R,17R)-3,16-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic 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 fdfa03e2-14f7-4cac-9949-cdb8f8d8627e
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives > Dihydroxy bile acids, alcohols and derivatives
IUPAC Name (2R)-2-[(3S,10S,13R,14R,16R,17R)-3,16-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
SMILES (Canonical) CC(C)C(=C)CCC(C1C(CC2(C1(CC=C3C2=CCC4C3(CCC(C4(C)C)O)C)C)C)O)C(=O)O
SMILES (Isomeric) CC(C)C(=C)CC[C@H]([C@H]1[C@@H](C[C@@]2([C@@]1(CC=C3C2=CCC4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C)O)C(=O)O
InChI InChI=1S/C31H48O4/c1-18(2)19(3)9-10-20(27(34)35)26-23(32)17-31(8)22-11-12-24-28(4,5)25(33)14-15-29(24,6)21(22)13-16-30(26,31)7/h11,13,18,20,23-26,32-33H,3,9-10,12,14-17H2,1-2,4-8H3,(H,34,35)/t20-,23-,24?,25+,26+,29-,30-,31+/m1/s1
InChI Key LADJWZMBZBVBSB-DWSVKRSBSA-N
Popularity 8 references in papers

Physical and Chemical Properties

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Molecular Formula C31H48O4
Molecular Weight 484.70 g/mol
Exact Mass 484.35526001 g/mol
Topological Polar Surface Area (TPSA) 77.80 Ų
XlogP 6.40
Atomic LogP (AlogP) 6.54
H-Bond Acceptor 3
H-Bond Donor 3
Rotatable Bonds 6

Synonyms

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(2R)-2-[(3S,10S,13R,14R,16R,17R)-3,16-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
DTXSID20986918
3,16-Dihydroxy-24-methylidenelanosta-7,9(11)-dien-21-oic acid
Lanosta-7,9(11)-dien-21-oic acid, 3,16-dihydroxy-24-methylene-, (3beta,16alpha)-

2D Structure

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2D Structure of (2R)-2-[(3S,10S,13R,14R,16R,17R)-3,16-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9941 99.41%
Caco-2 + 0.9312 93.12%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.8143 81.43%
OATP2B1 inhibitior - 0.8599 85.99%
OATP1B1 inhibitior + 0.8836 88.36%
OATP1B3 inhibitior - 0.4538 45.38%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior + 0.7618 76.18%
P-glycoprotein inhibitior - 0.5088 50.88%
P-glycoprotein substrate - 0.6160 61.60%
CYP3A4 substrate + 0.6515 65.15%
CYP2C9 substrate - 0.8398 83.98%
CYP2D6 substrate - 0.8724 87.24%
CYP3A4 inhibition - 0.8247 82.47%
CYP2C9 inhibition - 0.9198 91.98%
CYP2C19 inhibition - 0.9312 93.12%
CYP2D6 inhibition - 0.9565 95.65%
CYP1A2 inhibition - 0.9365 93.65%
CYP2C8 inhibition + 0.4467 44.67%
CYP inhibitory promiscuity - 0.8550 85.50%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7062 70.62%
Eye corrosion - 0.9948 99.48%
Eye irritation - 0.9409 94.09%
Skin irritation + 0.6976 69.76%
Skin corrosion - 0.9527 95.27%
Ames mutagenesis - 0.8115 81.15%
Human Ether-a-go-go-Related Gene inhibition - 0.5058 50.58%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.6093 60.93%
skin sensitisation - 0.6403 64.03%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9750 97.50%
Nephrotoxicity - 0.8216 82.16%
Acute Oral Toxicity (c) III 0.5766 57.66%
Estrogen receptor binding + 0.7437 74.37%
Androgen receptor binding + 0.7321 73.21%
Thyroid receptor binding + 0.6987 69.87%
Glucocorticoid receptor binding + 0.7561 75.61%
Aromatase binding + 0.7105 71.05%
PPAR gamma + 0.5579 55.79%
Honey bee toxicity - 0.7895 78.95%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.6800 68.00%
Fish aquatic toxicity + 1.0000 100.00%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4040 P28482 MAP kinase ERK2 99.11% 83.82%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.33% 96.09%
CHEMBL221 P23219 Cyclooxygenase-1 96.62% 90.17%
CHEMBL2581 P07339 Cathepsin D 96.07% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.91% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.41% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.32% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.77% 97.09%
CHEMBL4227 P25090 Lipoxin A4 receptor 86.89% 100.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.54% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.71% 100.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 85.15% 93.56%
CHEMBL340 P08684 Cytochrome P450 3A4 80.46% 91.19%
CHEMBL218 P21554 Cannabinoid CB1 receptor 80.27% 96.61%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 216251
LOTUS LTS0227324
wikiData Q72461906