[(1S)-1-[(3S,5S,8S,9S,10S,12R,13S,14R,17S)-12-acetyloxy-3,8,14,17-tetrahydroxy-10-methyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl] pyridine-2-carboxylate

Details

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Internal ID c400d37e-3bb6-4b98-9b1a-9eb296beb0ce
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid esters
IUPAC Name [(1S)-1-[(3S,5S,8S,9S,10S,12R,13S,14R,17S)-12-acetyloxy-3,8,14,17-tetrahydroxy-10-methyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl] pyridine-2-carboxylate
SMILES (Canonical) CC(C1(CCC2(C1C(CC3C2(CCC4C3(CCC(C4)O)C)O)OC(=O)C)O)O)OC(=O)C5=CC=CC=N5
SMILES (Isomeric) C[C@@H]([C@@]1(CC[C@]2([C@H]1[C@@H](C[C@@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4)O)C)O)OC(=O)C)O)O)OC(=O)C5=CC=CC=N5
InChI InChI=1S/C28H39NO8/c1-16(36-24(32)20-6-4-5-13-29-20)26(33)11-12-28(35)23(26)21(37-17(2)30)15-22-25(3)9-8-19(31)14-18(25)7-10-27(22,28)34/h4-6,13,16,18-19,21-23,31,33-35H,7-12,14-15H2,1-3H3/t16-,18-,19-,21+,22-,23-,25-,26+,27-,28+/m0/s1
InChI Key AJEYBRIZNAXITC-HLGYPHQCSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H39NO8
Molecular Weight 517.60 g/mol
Exact Mass 517.26756720 g/mol
Topological Polar Surface Area (TPSA) 146.00 Ų
XlogP 1.80
Atomic LogP (AlogP) 2.14
H-Bond Acceptor 9
H-Bond Donor 4
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S)-1-[(3S,5S,8S,9S,10S,12R,13S,14R,17S)-12-acetyloxy-3,8,14,17-tetrahydroxy-10-methyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl] pyridine-2-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8080 80.80%
Caco-2 - 0.8503 85.03%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.5586 55.86%
OATP2B1 inhibitior - 0.8599 85.99%
OATP1B1 inhibitior + 0.8865 88.65%
OATP1B3 inhibitior + 0.9223 92.23%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.8571 85.71%
BSEP inhibitior + 0.9538 95.38%
P-glycoprotein inhibitior - 0.5227 52.27%
P-glycoprotein substrate + 0.5590 55.90%
CYP3A4 substrate + 0.7171 71.71%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8619 86.19%
CYP3A4 inhibition - 0.8618 86.18%
CYP2C9 inhibition - 0.9248 92.48%
CYP2C19 inhibition - 0.8672 86.72%
CYP2D6 inhibition - 0.9394 93.94%
CYP1A2 inhibition - 0.7111 71.11%
CYP2C8 inhibition + 0.6339 63.39%
CYP inhibitory promiscuity - 0.9505 95.05%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6637 66.37%
Eye corrosion - 0.9923 99.23%
Eye irritation - 0.9446 94.46%
Skin irritation - 0.6526 65.26%
Skin corrosion - 0.9208 92.08%
Ames mutagenesis - 0.6570 65.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4175 41.75%
Micronuclear - 0.6400 64.00%
Hepatotoxicity - 0.5470 54.70%
skin sensitisation - 0.8843 88.43%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity - 0.6990 69.90%
Acute Oral Toxicity (c) III 0.5339 53.39%
Estrogen receptor binding + 0.7600 76.00%
Androgen receptor binding + 0.6803 68.03%
Thyroid receptor binding - 0.5462 54.62%
Glucocorticoid receptor binding + 0.5843 58.43%
Aromatase binding + 0.6620 66.20%
PPAR gamma + 0.5418 54.18%
Honey bee toxicity - 0.7716 77.16%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5255 52.55%
Fish aquatic toxicity + 0.8594 85.94%

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
CHEMBL221 P23219 Cyclooxygenase-1 98.78% 90.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.07% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.84% 91.11%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 96.50% 94.62%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 95.21% 94.08%
CHEMBL2581 P07339 Cathepsin D 92.40% 98.95%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 91.01% 94.23%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.57% 94.45%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 89.34% 82.69%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 86.89% 94.97%
CHEMBL2782 P35610 Acyl coenzyme A:cholesterol acyltransferase 1 85.83% 91.65%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.78% 86.33%
CHEMBL226 P30542 Adenosine A1 receptor 85.37% 95.93%
CHEMBL284 P27487 Dipeptidyl peptidase IV 84.90% 95.69%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 84.63% 89.44%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.05% 99.23%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 83.87% 100.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.83% 95.89%
CHEMBL2378 P30307 Dual specificity phosphatase Cdc25C 82.53% 96.67%
CHEMBL5028 O14672 ADAM10 81.48% 97.50%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 81.30% 89.67%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 81.04% 93.10%

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.
Anomodon attenuatus
Isothecium subdiversiforme
Marsdenia rostrata

Cross-Links

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PubChem 162922668
LOTUS LTS0103899
wikiData Q105196510