PlantaeDB Logo
Login Sign-up

(3R,4S,6R)-4-(2-hydroxyethyl)-6-[(1R)-1-hydroxy-1-[(2S,3R,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]ethyl]-3-methyloxan-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

Top
Internal ID f2a459c4-89c2-4bee-927d-862871c3ae7b
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (3R,4S,6R)-4-(2-hydroxyethyl)-6-[(1R)-1-hydroxy-1-[(2S,3R,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]ethyl]-3-methyloxan-2-one
SMILES (Canonical) CC1C(CC(OC1=O)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)CCO
SMILES (Isomeric) C[C@@H]1[C@H](C[C@@H](OC1=O)[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)CCO
InChI InChI=1S/C29H44O8/c1-15-16(7-10-30)11-24(37-25(15)34)28(4,35)23-6-9-29(36)18-12-20(31)19-13-21(32)22(33)14-26(19,2)17(18)5-8-27(23,29)3/h12,15-17,19,21-24,30,32-33,35-36H,5-11,13-14H2,1-4H3/t15-,16+,17+,19+,21-,22+,23+,24-,26-,27-,28-,29-/m1/s1
InChI Key IUYYKOCXIXIADY-TZYAEJFRSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C29H44O8
Molecular Weight 520.70 g/mol
Exact Mass 520.30361836 g/mol
Topological Polar Surface Area (TPSA) 145.00 Ų
XlogP 1.00
Atomic LogP (AlogP) 1.89
H-Bond Acceptor 8
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (3R,4S,6R)-4-(2-hydroxyethyl)-6-[(1R)-1-hydroxy-1-[(2S,3R,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]ethyl]-3-methyloxan-2-one

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9368 93.68%
Caco-2 - 0.6703 67.03%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability + 0.5286 52.86%
Subcellular localzation Mitochondria 0.8673 86.73%
OATP2B1 inhibitior - 0.5711 57.11%
OATP1B1 inhibitior + 0.8645 86.45%
OATP1B3 inhibitior + 0.9231 92.31%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5122 51.22%
BSEP inhibitior + 0.8243 82.43%
P-glycoprotein inhibitior - 0.5249 52.49%
P-glycoprotein substrate + 0.5907 59.07%
CYP3A4 substrate + 0.6987 69.87%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9056 90.56%
CYP3A4 inhibition - 0.6471 64.71%
CYP2C9 inhibition - 0.9161 91.61%
CYP2C19 inhibition - 0.9326 93.26%
CYP2D6 inhibition - 0.9467 94.67%
CYP1A2 inhibition - 0.8739 87.39%
CYP2C8 inhibition - 0.5663 56.63%
CYP inhibitory promiscuity - 0.9592 95.92%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6332 63.32%
Eye corrosion - 0.9924 99.24%
Eye irritation - 0.9434 94.34%
Skin irritation + 0.6658 66.58%
Skin corrosion - 0.9398 93.98%
Ames mutagenesis - 0.6770 67.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4212 42.12%
Micronuclear - 0.8100 81.00%
Hepatotoxicity + 0.5266 52.66%
skin sensitisation - 0.9189 91.89%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.8375 83.75%
Nephrotoxicity - 0.8209 82.09%
Acute Oral Toxicity (c) III 0.6223 62.23%
Estrogen receptor binding + 0.7342 73.42%
Androgen receptor binding + 0.7593 75.93%
Thyroid receptor binding - 0.5240 52.40%
Glucocorticoid receptor binding + 0.7378 73.78%
Aromatase binding + 0.6665 66.65%
PPAR gamma + 0.5365 53.65%
Honey bee toxicity - 0.8202 82.02%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9717 97.17%

Targets

Top

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 99.38% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.81% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.35% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.74% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.84% 96.09%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 92.72% 86.92%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.72% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.61% 100.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 88.93% 91.07%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.60% 95.89%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 86.82% 82.69%
CHEMBL1951 P21397 Monoamine oxidase A 86.37% 91.49%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 85.30% 94.78%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.97% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.81% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.59% 89.00%
CHEMBL2581 P07339 Cathepsin D 83.66% 98.95%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.68% 97.14%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.19% 92.62%
CHEMBL5555 O00767 Acyl-CoA desaturase 81.92% 97.50%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 81.14% 96.90%
CHEMBL218 P21554 Cannabinoid CB1 receptor 81.10% 96.61%
CHEMBL4040 P28482 MAP kinase ERK2 80.38% 83.82%

Plants that contains it

Top
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

Top
PubChem 162959785
LOTUS LTS0188561
wikiData Q105120931