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[(3S,5R,6R,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3,5-dihydroxy-10,13-dimethyl-1,2,3,4,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-yl] acetate

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 ea5662b7-a381-4b56-a02c-2ac03f4290d1
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Ergostane steroids > Ergosterols and derivatives
IUPAC Name [(3S,5R,6R,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3,5-dihydroxy-10,13-dimethyl-1,2,3,4,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-yl] acetate
SMILES (Canonical) CC(C)C(C)C=CC(C)C1CCC2C1(CCC3C2=CC(C4(C3(CCC(C4)O)C)O)OC(=O)C)C
SMILES (Isomeric) C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3C2=C[C@H]([C@@]4([C@@]3(CC[C@@H](C4)O)C)O)OC(=O)C)C
InChI InChI=1S/C30H48O4/c1-18(2)19(3)8-9-20(4)24-10-11-25-23-16-27(34-21(5)31)30(33)17-22(32)12-15-29(30,7)26(23)13-14-28(24,25)6/h8-9,16,18-20,22,24-27,32-33H,10-15,17H2,1-7H3/b9-8+/t19-,20+,22-,24+,25-,26-,27+,28+,29+,30-/m0/s1
InChI Key WOOGXTMIIGJREK-ITQKUNLLSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C30H48O4
Molecular Weight 472.70 g/mol
Exact Mass 472.35526001 g/mol
Topological Polar Surface Area (TPSA) 66.80 Ų
XlogP 6.20
Atomic LogP (AlogP) 6.07
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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(22E)-5alpha-Ergosta-7,22-diene-3beta,5,6beta-triol 6-acetate

2D Structure

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2D Structure of [(3S,5R,6R,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3,5-dihydroxy-10,13-dimethyl-1,2,3,4,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9887 98.87%
Caco-2 - 0.6104 61.04%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.8084 80.84%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7943 79.43%
OATP1B3 inhibitior - 0.3754 37.54%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7071 70.71%
BSEP inhibitior + 0.6797 67.97%
P-glycoprotein inhibitior - 0.4669 46.69%
P-glycoprotein substrate - 0.5636 56.36%
CYP3A4 substrate + 0.7013 70.13%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8733 87.33%
CYP3A4 inhibition - 0.8810 88.10%
CYP2C9 inhibition - 0.7391 73.91%
CYP2C19 inhibition - 0.8085 80.85%
CYP2D6 inhibition - 0.9467 94.67%
CYP1A2 inhibition - 0.7802 78.02%
CYP2C8 inhibition - 0.6573 65.73%
CYP inhibitory promiscuity - 0.8901 89.01%
UGT catelyzed + 0.6362 63.62%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6201 62.01%
Eye corrosion - 0.9932 99.32%
Eye irritation - 0.9576 95.76%
Skin irritation + 0.6577 65.77%
Skin corrosion - 0.9419 94.19%
Ames mutagenesis - 0.7070 70.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4564 45.64%
Micronuclear - 0.8000 80.00%
Hepatotoxicity - 0.6542 65.42%
skin sensitisation - 0.7765 77.65%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.9889 98.89%
Mitochondrial toxicity + 0.9375 93.75%
Nephrotoxicity - 0.7446 74.46%
Acute Oral Toxicity (c) I 0.5828 58.28%
Estrogen receptor binding + 0.8459 84.59%
Androgen receptor binding + 0.6367 63.67%
Thyroid receptor binding + 0.6194 61.94%
Glucocorticoid receptor binding + 0.7925 79.25%
Aromatase binding + 0.6124 61.24%
PPAR gamma + 0.5886 58.86%
Honey bee toxicity - 0.7255 72.55%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity + 0.9942 99.42%

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
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 97.99% 82.69%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.83% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.53% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.30% 94.45%
CHEMBL2581 P07339 Cathepsin D 92.20% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.84% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.97% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 90.83% 95.89%
CHEMBL221 P23219 Cyclooxygenase-1 88.53% 90.17%
CHEMBL3359 P21462 Formyl peptide receptor 1 86.35% 93.56%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.21% 95.89%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.69% 97.09%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 85.64% 97.14%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.13% 91.07%
CHEMBL1937 Q92769 Histone deacetylase 2 84.07% 94.75%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 84.06% 94.23%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.88% 100.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.56% 100.00%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 82.41% 94.97%
CHEMBL5028 O14672 ADAM10 81.70% 97.50%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.67% 86.33%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 81.38% 94.08%

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.
Rhodiola rosea

Cross-Links

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PubChem 100997595
NPASS NPC77531
LOTUS LTS0272645
wikiData Q105309620