[(1S,3S,4S,4aR,8aR)-4-hydroxy-3,4a,8,8-tetramethyl-4-[2-(5-oxo-1,2-dihydropyrrol-4-yl)ethyl]-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate

Details

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Internal ID cbf0bdb6-3c66-4e9b-9fc3-0b8d88786a03
Taxonomy Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Tertiary alcohols
IUPAC Name [(1S,3S,4S,4aR,8aR)-4-hydroxy-3,4a,8,8-tetramethyl-4-[2-(5-oxo-1,2-dihydropyrrol-4-yl)ethyl]-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate
SMILES (Canonical) CC1CC(C2C(CCCC2(C1(CCC3=CCNC3=O)O)C)(C)C)OC(=O)C
SMILES (Isomeric) C[C@H]1C[C@@H]([C@H]2[C@]([C@@]1(CCC3=CCNC3=O)O)(CCCC2(C)C)C)OC(=O)C
InChI InChI=1S/C22H35NO4/c1-14-13-17(27-15(2)24)18-20(3,4)9-6-10-21(18,5)22(14,26)11-7-16-8-12-23-19(16)25/h8,14,17-18,26H,6-7,9-13H2,1-5H3,(H,23,25)/t14-,17-,18+,21+,22-/m0/s1
InChI Key LTVWDGPECBUWSM-QXGXDSNISA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C22H35NO4
Molecular Weight 377.50 g/mol
Exact Mass 377.25660860 g/mol
Topological Polar Surface Area (TPSA) 75.60 Ų
XlogP 3.70
Atomic LogP (AlogP) 3.36
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,3S,4S,4aR,8aR)-4-hydroxy-3,4a,8,8-tetramethyl-4-[2-(5-oxo-1,2-dihydropyrrol-4-yl)ethyl]-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-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 + 0.9860 98.60%
Caco-2 - 0.5816 58.16%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.7728 77.28%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8406 84.06%
OATP1B3 inhibitior + 0.9109 91.09%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior - 0.4577 45.77%
P-glycoprotein inhibitior - 0.5170 51.70%
P-glycoprotein substrate + 0.5124 51.24%
CYP3A4 substrate + 0.6638 66.38%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9123 91.23%
CYP3A4 inhibition - 0.6003 60.03%
CYP2C9 inhibition - 0.7022 70.22%
CYP2C19 inhibition - 0.7975 79.75%
CYP2D6 inhibition - 0.9166 91.66%
CYP1A2 inhibition - 0.8473 84.73%
CYP2C8 inhibition + 0.4685 46.85%
CYP inhibitory promiscuity - 0.5321 53.21%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5680 56.80%
Eye corrosion - 0.9922 99.22%
Eye irritation - 0.9598 95.98%
Skin irritation - 0.6845 68.45%
Skin corrosion - 0.9381 93.81%
Ames mutagenesis - 0.5000 50.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5000 50.00%
Micronuclear + 0.5600 56.00%
Hepatotoxicity + 0.5178 51.78%
skin sensitisation - 0.8509 85.09%
Respiratory toxicity + 0.5111 51.11%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity - 0.5972 59.72%
Acute Oral Toxicity (c) III 0.6774 67.74%
Estrogen receptor binding + 0.7550 75.50%
Androgen receptor binding + 0.5930 59.30%
Thyroid receptor binding + 0.7368 73.68%
Glucocorticoid receptor binding + 0.8392 83.92%
Aromatase binding + 0.7135 71.35%
PPAR gamma + 0.5940 59.40%
Honey bee toxicity - 0.7921 79.21%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.9750 97.50%

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 99.24% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.24% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.03% 91.11%
CHEMBL2581 P07339 Cathepsin D 95.20% 98.95%
CHEMBL2996 Q05655 Protein kinase C delta 95.16% 97.79%
CHEMBL1937 Q92769 Histone deacetylase 2 94.95% 94.75%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.70% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.30% 97.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.83% 85.14%
CHEMBL255 P29275 Adenosine A2b receptor 87.24% 98.59%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.53% 86.33%
CHEMBL4208 P20618 Proteasome component C5 83.61% 90.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 83.57% 82.69%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 81.91% 91.03%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.39% 99.23%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 80.36% 94.08%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.32% 100.00%
CHEMBL2095226 P05556 Integrin alpha-5/beta-1 80.24% 96.39%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.07% 93.04%
CHEMBL1902 P62942 FK506-binding protein 1A 80.05% 97.05%

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.
Vitex agnus-castus

Cross-Links

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PubChem 163014727
LOTUS LTS0244862
wikiData Q105157211