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(3S,4S)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-6-oxo-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[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 2eee8d7f-4646-477d-bcd2-ce12e7deba53
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives
IUPAC Name (3S,4S)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-6-oxo-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]butyl]-3-methyloxolan-2-one
SMILES (Canonical) CC1C(COC1=O)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5(C4(CC(C(C5)O)O)C)O)C)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H](COC1=O)C[C@H]([C@@](C)([C@H]2CC[C@@]3([C@@]2(CC[C@H]4C3=CC(=O)[C@]5([C@@]4(C[C@@H]([C@@H](C5)O)O)C)O)C)O)O)O
InChI InChI=1S/C28H42O9/c1-14-15(13-37-23(14)33)9-21(31)26(4,34)20-6-8-27(35)17-10-22(32)28(36)12-19(30)18(29)11-25(28,3)16(17)5-7-24(20,27)2/h10,14-16,18-21,29-31,34-36H,5-9,11-13H2,1-4H3/t14-,15+,16-,18-,19+,20-,21+,24+,25+,26+,27+,28+/m0/s1
InChI Key AJPNSKWVBMZHRH-HDWGAXEUSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H42O9
Molecular Weight 522.60 g/mol
Exact Mass 522.28288291 g/mol
Topological Polar Surface Area (TPSA) 165.00 Ų
XlogP -0.20
Atomic LogP (AlogP) 0.62
H-Bond Acceptor 9
H-Bond Donor 6
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-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-6-oxo-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[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 - 0.7213 72.13%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability + 0.5286 52.86%
Subcellular localzation Mitochondria 0.8333 83.33%
OATP2B1 inhibitior - 0.5722 57.22%
OATP1B1 inhibitior + 0.8819 88.19%
OATP1B3 inhibitior + 0.9488 94.88%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5662 56.62%
BSEP inhibitior + 0.5651 56.51%
P-glycoprotein inhibitior - 0.5536 55.36%
P-glycoprotein substrate + 0.5857 58.57%
CYP3A4 substrate + 0.6794 67.94%
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 - 0.5989 59.89%
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 - 0.9349 93.49%
Skin irritation + 0.7012 70.12%
Skin corrosion - 0.9336 93.36%
Ames mutagenesis - 0.6270 62.70%
Human Ether-a-go-go-Related Gene inhibition - 0.3938 39.38%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.5402 54.02%
skin sensitisation - 0.9236 92.36%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity - 0.8451 84.51%
Acute Oral Toxicity (c) III 0.5792 57.92%
Estrogen receptor binding + 0.7548 75.48%
Androgen receptor binding + 0.7714 77.14%
Thyroid receptor binding + 0.5220 52.20%
Glucocorticoid receptor binding + 0.7584 75.84%
Aromatase binding + 0.7132 71.32%
PPAR gamma - 0.5771 57.71%
Honey bee toxicity - 0.8213 82.13%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5900 59.00%
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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 99.62% 85.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 99.24% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.95% 91.11%
CHEMBL2581 P07339 Cathepsin D 95.20% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.50% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.17% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.10% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.96% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.90% 89.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 87.49% 97.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.10% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.95% 95.89%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 84.92% 82.69%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 83.30% 94.78%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.82% 86.33%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 82.77% 96.77%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.61% 100.00%

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 14693881
LOTUS LTS0257081
wikiData Q104391592