(2S,3R,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one

Details

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Internal ID 558b4509-a5a9-4129-ad04-1e8c9840a31a
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives > Pentahydroxy bile acids, alcohols and derivatives
IUPAC Name (2S,3R,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
SMILES (Canonical) CC12CCC3C(=CC(=O)C4C3(CC(C(C4)OC5C(C(C(C(O5)CO)O)O)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O
SMILES (Isomeric) C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O[C@@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O)O)O)O)C)[C@@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O
InChI InChI=1S/C33H54O12/c1-29(2,41)9-8-24(37)32(5,42)23-7-11-33(43)17-12-19(35)18-13-21(44-28-27(40)26(39)25(38)22(15-34)45-28)20(36)14-30(18,3)16(17)6-10-31(23,33)4/h12,16,18,20-28,34,36-43H,6-11,13-15H2,1-5H3/t16-,18-,20-,21+,22+,23-,24+,25-,26-,27+,28-,30+,31+,32+,33+/m0/s1
InChI Key APFXLSITBUTSAO-SDNJJZGQSA-N
Popularity 6 references in papers

Physical and Chemical Properties

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Molecular Formula C33H54O12
Molecular Weight 642.80 g/mol
Exact Mass 642.36152715 g/mol
Topological Polar Surface Area (TPSA) 218.00 Ų
XlogP -1.10
Atomic LogP (AlogP) -0.32
H-Bond Acceptor 12
H-Bond Donor 9
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3R,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9026 90.26%
Caco-2 - 0.8282 82.82%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.8857 88.57%
Subcellular localzation Mitochondria 0.8474 84.74%
OATP2B1 inhibitior - 0.7228 72.28%
OATP1B1 inhibitior + 0.8893 88.93%
OATP1B3 inhibitior - 0.2724 27.24%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.6568 65.68%
BSEP inhibitior + 0.7049 70.49%
P-glycoprotein inhibitior + 0.6659 66.59%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.7258 72.58%
CYP2C9 substrate - 0.8067 80.67%
CYP2D6 substrate - 0.8910 89.10%
CYP3A4 inhibition - 0.8752 87.52%
CYP2C9 inhibition - 0.8084 80.84%
CYP2C19 inhibition - 0.9022 90.22%
CYP2D6 inhibition - 0.9331 93.31%
CYP1A2 inhibition - 0.8266 82.66%
CYP2C8 inhibition + 0.5574 55.74%
CYP inhibitory promiscuity - 0.9107 91.07%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6947 69.47%
Eye corrosion - 0.9912 99.12%
Eye irritation - 0.9258 92.58%
Skin irritation + 0.5185 51.85%
Skin corrosion - 0.9448 94.48%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7125 71.25%
Micronuclear - 0.8300 83.00%
Hepatotoxicity - 0.5463 54.63%
skin sensitisation - 0.9059 90.59%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity - 0.8100 81.00%
Acute Oral Toxicity (c) III 0.6684 66.84%
Estrogen receptor binding + 0.7355 73.55%
Androgen receptor binding + 0.7448 74.48%
Thyroid receptor binding - 0.5369 53.69%
Glucocorticoid receptor binding + 0.6278 62.78%
Aromatase binding + 0.6439 64.39%
PPAR gamma + 0.6007 60.07%
Honey bee toxicity - 0.7231 72.31%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9645 96.45%

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 99.58% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.87% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.34% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 97.21% 97.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 95.05% 96.61%
CHEMBL2581 P07339 Cathepsin D 93.79% 98.95%
CHEMBL220 P22303 Acetylcholinesterase 93.50% 94.45%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 92.60% 96.21%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.46% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.00% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 91.75% 95.89%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 91.18% 94.78%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.44% 100.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 89.83% 97.14%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 89.28% 86.92%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 88.93% 94.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.11% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.75% 94.45%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 85.13% 100.00%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 84.11% 97.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.76% 89.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.68% 91.07%
CHEMBL2265 P23141 Acyl coenzyme A:cholesterol acyltransferase 82.43% 85.94%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.90% 95.89%
CHEMBL3922 P50579 Methionine aminopeptidase 2 81.90% 97.28%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 81.71% 95.50%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 80.83% 100.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.55% 94.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.47% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.14% 93.04%

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.
Silene brahuica
Silene turkestanica
Silene viridiflora

Cross-Links

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PubChem 21768882
LOTUS LTS0058606
wikiData Q104252453