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(3S,4S)-4-[(3R)-3-hydroxy-2-oxo-3-[(2S,3R,5R,9R,10R,12R,13S,14R,17S)-2,3,12,14-tetrahydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]butyl]-3-methyloxolan-2-one

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 e0d1a6a0-24a4-4608-a8cc-7d2b236a16ff
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 (3S,4S)-4-[(3R)-3-hydroxy-2-oxo-3-[(2S,3R,5R,9R,10R,12R,13S,14R,17S)-2,3,12,14-tetrahydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]butyl]-3-methyloxolan-2-one
SMILES (Canonical) CC1C(COC1=O)CC(=O)C(C)(C2CCC3(C2(C(CC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)O)C)O)O
SMILES (Isomeric) C[C@H]1[C@@H](COC1=O)CC(=O)[C@@](C)([C@H]2CC[C@@]3([C@@]2([C@@H](C[C@H]4C3=CC(=O)[C@H]5[C@@]4(C[C@@H]([C@@H](C5)O)O)C)O)C)O)O
InChI InChI=1S/C28H40O9/c1-13-14(12-37-24(13)34)7-23(33)27(4,35)21-5-6-28(36)16-8-18(29)17-9-19(30)20(31)11-25(17,2)15(16)10-22(32)26(21,28)3/h8,13-15,17,19-22,30-32,35-36H,5-7,9-12H2,1-4H3/t13-,14+,15-,17-,19+,20-,21-,22+,25+,26-,27+,28+/m0/s1
InChI Key UYTJADWYDZXNQA-LDVVGOFSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H40O9
Molecular Weight 520.60 g/mol
Exact Mass 520.26723285 g/mol
Topological Polar Surface Area (TPSA) 162.00 Ų
XlogP -0.60
Atomic LogP (AlogP) 0.68
H-Bond Acceptor 9
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3S,4S)-4-[(3R)-3-hydroxy-2-oxo-3-[(2S,3R,5R,9R,10R,12R,13S,14R,17S)-2,3,12,14-tetrahydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]butyl]-3-methyloxolan-2-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9533 95.33%
Caco-2 - 0.7457 74.57%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability + 0.5143 51.43%
Subcellular localzation Mitochondria 0.8333 83.33%
OATP2B1 inhibitior - 0.5693 56.93%
OATP1B1 inhibitior + 0.8643 86.43%
OATP1B3 inhibitior + 0.9488 94.88%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5662 56.62%
BSEP inhibitior + 0.6549 65.49%
P-glycoprotein inhibitior - 0.4616 46.16%
P-glycoprotein substrate + 0.6584 65.84%
CYP3A4 substrate + 0.6702 67.02%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9048 90.48%
CYP3A4 inhibition - 0.7332 73.32%
CYP2C9 inhibition - 0.8652 86.52%
CYP2C19 inhibition - 0.9027 90.27%
CYP2D6 inhibition - 0.9483 94.83%
CYP1A2 inhibition - 0.8930 89.30%
CYP2C8 inhibition - 0.6175 61.75%
CYP inhibitory promiscuity - 0.9457 94.57%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4907 49.07%
Eye corrosion - 0.9911 99.11%
Eye irritation - 0.9406 94.06%
Skin irritation + 0.7012 70.12%
Skin corrosion - 0.9336 93.36%
Ames mutagenesis - 0.6770 67.70%
Human Ether-a-go-go-Related Gene inhibition - 0.5000 50.00%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.5282 52.82%
skin sensitisation - 0.9236 92.36%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity - 0.8780 87.80%
Acute Oral Toxicity (c) III 0.5792 57.92%
Estrogen receptor binding + 0.6938 69.38%
Androgen receptor binding + 0.7582 75.82%
Thyroid receptor binding + 0.5355 53.55%
Glucocorticoid receptor binding + 0.7616 76.16%
Aromatase binding + 0.7040 70.40%
PPAR gamma + 0.5391 53.91%
Honey bee toxicity - 0.8025 80.25%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9898 98.98%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 99.03% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.28% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.39% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.12% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.05% 95.56%
CHEMBL2581 P07339 Cathepsin D 94.73% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.44% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.37% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.32% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.27% 89.00%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 88.59% 96.90%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 87.98% 82.69%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 87.88% 96.77%
CHEMBL226 P30542 Adenosine A1 receptor 86.81% 95.93%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 85.07% 97.14%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 83.94% 86.92%
CHEMBL4588 P22894 Matrix metalloproteinase 8 83.62% 94.66%
CHEMBL4040 P28482 MAP kinase ERK2 81.66% 83.82%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.64% 86.33%

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.
Ajuga reptans

Cross-Links

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PubChem 162982727
LOTUS LTS0136426
wikiData Q105281928