(3S,4aR,6aR,6aR,6bR,8aS,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,6a,7,8,9,12,12a,13,14,14a-tetradecahydro-1H-picen-3-ol

Details

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Internal ID 32e3c12f-3524-4747-9f27-6b05bb808953
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (3S,4aR,6aR,6aR,6bR,8aS,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,6a,7,8,9,12,12a,13,14,14a-tetradecahydro-1H-picen-3-ol
SMILES (Canonical) CC1C2C3CCC4C5(CCC(C(C5CCC4(C3(CCC2(CC=C1C)C)C)C)(C)C)O)C
SMILES (Isomeric) C[C@H]1[C@@H]2[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC[C@]2(CC=C1C)C)C)C)(C)C)O)C
InChI InChI=1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h11,20-25,31H,9-10,12-18H2,1-8H3/t20-,21-,22+,23-,24+,25-,27-,28+,29-,30-/m1/s1
InChI Key NGFFRJBGMSPDMS-ZJJHUPNDSA-N
Popularity 15 references in papers

Physical and Chemical Properties

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Molecular Formula C30H50O
Molecular Weight 426.70 g/mol
Exact Mass 426.386166214 g/mol
Topological Polar Surface Area (TPSA) 20.20 Ų
XlogP 8.90
Atomic LogP (AlogP) 8.02
H-Bond Acceptor 1
H-Bond Donor 1
Rotatable Bonds 0

Synonyms

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464-98-2
EX-A6771
HY-N1555
AKOS040762231
CS-0017104
20-Taraxasten-3-ol; psi-Taraxasterol; -Taraxasterol

2D Structure

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2D Structure of (3S,4aR,6aR,6aR,6bR,8aS,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,6a,7,8,9,12,12a,13,14,14a-tetradecahydro-1H-picen-3-ol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9974 99.74%
Caco-2 + 0.5374 53.74%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.4847 48.47%
OATP2B1 inhibitior - 0.8659 86.59%
OATP1B1 inhibitior + 0.9128 91.28%
OATP1B3 inhibitior + 0.9335 93.35%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior + 0.8875 88.75%
P-glycoprotein inhibitior - 0.7363 73.63%
P-glycoprotein substrate - 0.8345 83.45%
CYP3A4 substrate + 0.6816 68.16%
CYP2C9 substrate - 0.6165 61.65%
CYP2D6 substrate - 0.7040 70.40%
CYP3A4 inhibition - 0.8040 80.40%
CYP2C9 inhibition - 0.8039 80.39%
CYP2C19 inhibition - 0.6920 69.20%
CYP2D6 inhibition - 0.9487 94.87%
CYP1A2 inhibition - 0.8479 84.79%
CYP2C8 inhibition - 0.6234 62.34%
CYP inhibitory promiscuity - 0.7935 79.35%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9100 91.00%
Carcinogenicity (trinary) Non-required 0.5859 58.59%
Eye corrosion - 0.9859 98.59%
Eye irritation - 0.9443 94.43%
Skin irritation + 0.6931 69.31%
Skin corrosion - 0.9484 94.84%
Ames mutagenesis - 0.7700 77.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7202 72.02%
Micronuclear - 0.9800 98.00%
Hepatotoxicity - 0.7834 78.34%
skin sensitisation + 0.7035 70.35%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity - 0.8888 88.88%
Acute Oral Toxicity (c) III 0.8508 85.08%
Estrogen receptor binding + 0.8876 88.76%
Androgen receptor binding + 0.7340 73.40%
Thyroid receptor binding + 0.6973 69.73%
Glucocorticoid receptor binding + 0.8008 80.08%
Aromatase binding + 0.7439 74.39%
PPAR gamma + 0.5408 54.08%
Honey bee toxicity - 0.8042 80.42%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.6900 69.00%
Fish aquatic toxicity + 0.9860 98.60%

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
CHEMBL241 Q14432 Phosphodiesterase 3A 91.83% 92.94%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.99% 96.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.73% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.28% 95.89%
CHEMBL218 P21554 Cannabinoid CB1 receptor 86.06% 96.61%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.97% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 85.70% 90.17%
CHEMBL1871 P10275 Androgen Receptor 84.10% 96.43%
CHEMBL2581 P07339 Cathepsin D 84.00% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.90% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.86% 97.25%
CHEMBL1937 Q92769 Histone deacetylase 2 81.86% 94.75%
CHEMBL4803 P29474 Nitric-oxide synthase, endothelial 81.08% 86.00%
CHEMBL2996 Q05655 Protein kinase C delta 80.13% 97.79%

Cross-Links

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PubChem 12305110
NPASS NPC126874
LOTUS LTS0235786
wikiData Q105178871