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(3S,4S)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3S,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-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 6cdf5af5-0049-404b-9a0b-d2c4207c9b8c
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-[(2R,3R)-2,3-dihydroxy-3-[(2S,3S,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-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(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)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@H]5[C@@]4(C[C@@H]([C@H](C5)O)O)C)C)O)O)O
InChI InChI=1S/C28H42O8/c1-14-15(13-36-24(14)33)9-23(32)27(4,34)22-6-8-28(35)17-10-19(29)18-11-20(30)21(31)12-25(18,2)16(17)5-7-26(22,28)3/h10,14-16,18,20-23,30-32,34-35H,5-9,11-13H2,1-4H3/t14-,15+,16-,18-,20-,21-,22-,23+,25+,26+,27+,28+/m0/s1
InChI Key KIUYPOUMVLICAJ-APNLOSGJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H42O8
Molecular Weight 506.60 g/mol
Exact Mass 506.28796829 g/mol
Topological Polar Surface Area (TPSA) 145.00 Ų
XlogP 0.60
Atomic LogP (AlogP) 1.50
H-Bond Acceptor 8
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-[(2R,3R)-2,3-dihydroxy-3-[(2S,3S,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-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 + 0.9785 97.85%
Caco-2 - 0.6916 69.16%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability + 0.5429 54.29%
Subcellular localzation Mitochondria 0.8754 87.54%
OATP2B1 inhibitior - 0.5689 56.89%
OATP1B1 inhibitior + 0.8935 89.35%
OATP1B3 inhibitior + 0.9604 96.04%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5095 50.95%
BSEP inhibitior + 0.6813 68.13%
P-glycoprotein inhibitior - 0.5719 57.19%
P-glycoprotein substrate + 0.6380 63.80%
CYP3A4 substrate + 0.6913 69.13%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9048 90.48%
CYP3A4 inhibition - 0.5135 51.35%
CYP2C9 inhibition - 0.8558 85.58%
CYP2C19 inhibition - 0.8928 89.28%
CYP2D6 inhibition - 0.9305 93.05%
CYP1A2 inhibition - 0.8677 86.77%
CYP2C8 inhibition + 0.4481 44.81%
CYP inhibitory promiscuity - 0.9344 93.44%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4901 49.01%
Eye corrosion - 0.9921 99.21%
Eye irritation - 0.9400 94.00%
Skin irritation + 0.7114 71.14%
Skin corrosion - 0.9359 93.59%
Ames mutagenesis - 0.6170 61.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4375 43.75%
Micronuclear - 0.7900 79.00%
Hepatotoxicity + 0.5513 55.13%
skin sensitisation - 0.9111 91.11%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.8875 88.75%
Nephrotoxicity - 0.8668 86.68%
Acute Oral Toxicity (c) III 0.5079 50.79%
Estrogen receptor binding + 0.7350 73.50%
Androgen receptor binding + 0.7582 75.82%
Thyroid receptor binding + 0.5372 53.72%
Glucocorticoid receptor binding + 0.7532 75.32%
Aromatase binding + 0.7137 71.37%
PPAR gamma - 0.5386 53.86%
Honey bee toxicity - 0.7890 78.90%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9927 99.27%

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 99.62% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 99.59% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.01% 91.11%
CHEMBL2581 P07339 Cathepsin D 93.94% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.52% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.72% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.38% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.85% 95.56%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 91.08% 82.69%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.49% 89.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 87.22% 96.77%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 87.12% 94.78%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.99% 94.45%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.51% 97.14%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 86.49% 91.07%
CHEMBL218 P21554 Cannabinoid CB1 receptor 86.31% 96.61%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.59% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.32% 95.89%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 82.96% 86.92%
CHEMBL4040 P28482 MAP kinase ERK2 82.50% 83.82%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 80.14% 90.24%

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 162948022
LOTUS LTS0274814
wikiData Q105141692