(1S)-1-[(2S,4aS,4bS,5R,8aS)-5-hydroxy-2,4b,8,8-tetramethyl-3,4,4a,5,6,7,8a,9-octahydro-1H-phenanthren-2-yl]ethane-1,2-diol

Details

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Internal ID 53db9d92-a44b-4d7e-b0e3-84502e3859af
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name (1S)-1-[(2S,4aS,4bS,5R,8aS)-5-hydroxy-2,4b,8,8-tetramethyl-3,4,4a,5,6,7,8a,9-octahydro-1H-phenanthren-2-yl]ethane-1,2-diol
SMILES (Canonical) CC1(CCC(C2(C1CC=C3C2CCC(C3)(C)C(CO)O)C)O)C
SMILES (Isomeric) C[C@@]1(CC[C@H]2C(=CC[C@@H]3[C@@]2([C@@H](CCC3(C)C)O)C)C1)[C@@H](CO)O
InChI InChI=1S/C20H34O3/c1-18(2)9-8-16(22)20(4)14-7-10-19(3,17(23)12-21)11-13(14)5-6-15(18)20/h5,14-17,21-23H,6-12H2,1-4H3/t14-,15-,16+,17+,19-,20+/m0/s1
InChI Key RMRLASQFTPYVGV-YGPNDZQQSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C20H34O3
Molecular Weight 322.50 g/mol
Exact Mass 322.25079494 g/mol
Topological Polar Surface Area (TPSA) 60.70 Ų
XlogP 3.00
Atomic LogP (AlogP) 3.28
H-Bond Acceptor 3
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S)-1-[(2S,4aS,4bS,5R,8aS)-5-hydroxy-2,4b,8,8-tetramethyl-3,4,4a,5,6,7,8a,9-octahydro-1H-phenanthren-2-yl]ethane-1,2-diol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9923 99.23%
Caco-2 + 0.6389 63.89%
Blood Brain Barrier + 0.6885 68.85%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.7818 78.18%
OATP2B1 inhibitior - 0.8576 85.76%
OATP1B1 inhibitior + 0.9267 92.67%
OATP1B3 inhibitior + 0.9525 95.25%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.6083 60.83%
BSEP inhibitior - 0.6163 61.63%
P-glycoprotein inhibitior - 0.8657 86.57%
P-glycoprotein substrate - 0.7093 70.93%
CYP3A4 substrate + 0.5878 58.78%
CYP2C9 substrate - 0.6197 61.97%
CYP2D6 substrate - 0.7438 74.38%
CYP3A4 inhibition - 0.7785 77.85%
CYP2C9 inhibition - 0.8538 85.38%
CYP2C19 inhibition - 0.8556 85.56%
CYP2D6 inhibition - 0.9316 93.16%
CYP1A2 inhibition - 0.9009 90.09%
CYP2C8 inhibition - 0.7849 78.49%
CYP inhibitory promiscuity - 0.8579 85.79%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.7041 70.41%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.9393 93.93%
Skin irritation - 0.6197 61.97%
Skin corrosion - 0.9609 96.09%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4277 42.77%
Micronuclear - 0.9000 90.00%
Hepatotoxicity - 0.6946 69.46%
skin sensitisation - 0.7317 73.17%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity - 0.7467 74.67%
Acute Oral Toxicity (c) III 0.6985 69.85%
Estrogen receptor binding + 0.7372 73.72%
Androgen receptor binding + 0.5707 57.07%
Thyroid receptor binding + 0.7288 72.88%
Glucocorticoid receptor binding + 0.8242 82.42%
Aromatase binding + 0.6099 60.99%
PPAR gamma - 0.5324 53.24%
Honey bee toxicity - 0.8637 86.37%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6900 69.00%
Fish aquatic toxicity + 0.9725 97.25%

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
CHEMBL4040 P28482 MAP kinase ERK2 99.41% 83.82%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.70% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.41% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.03% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.15% 97.09%
CHEMBL2581 P07339 Cathepsin D 90.94% 98.95%
CHEMBL221 P23219 Cyclooxygenase-1 90.55% 90.17%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.50% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.71% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.32% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.87% 89.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.27% 100.00%
CHEMBL218 P21554 Cannabinoid CB1 receptor 80.22% 96.61%

Cross-Links

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PubChem 101202346
NPASS NPC29678
LOTUS LTS0165104
wikiData Q105241015