2,2,4-trimethyl-5-oxocyclohex-3-enecarboxylic acid - Compound Card

2,2,4-trimethyl-5-oxocyclohex-3-enecarboxylic acid

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2,2,4-trimethyl-5-oxocyclohex-3-enecarboxylic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC(=O)C1CC(=O)C(=CC1(C)C)C
InChI InChI=1S/C10H14O3/c1-6-5-10(2,3)7(9(12)13)4-8(6)11/h5,7H,4H2,1-3H3,(H,12,13)
InChIKey KFKGGMRELGBRAF-UHFFFAOYSA-N
Formula C10H14O3
HBA 2
HBD 1
MW 182.22
Rotatable Bonds 1
TPSA 54.37
LogP 1.63
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 13
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 182.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329

Showing of synonyms

  • Laid M (2011). Etude phytochimique d’une plante médicinale de l’Est Algérien (Artemisia herba alba).. PhD Thesis, 2011, Universite Mantouri-Constantine, Faculty of Science, Algeria. [View]
Pubchem: 21631037
Nmrshiftdb2: 20181362

No compound-protein relationship available.

Structure

SMILES: O=C1C=CCCC1

Level: 0

Mol. Weight: 182.22 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.33
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.39
Plasma Protein Binding
16.34
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.35
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.01
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.45
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.37
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
2.03
Rat (Acute)
1.91
Rat (Chronic Oral)
1.95
Fathead Minnow
3.69
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
278.12
Hydration Free Energy
-8.3
Log(D) at pH=7.4
-0.39
Log(P)
1.42
Log S
-1.49
Log(Vapor Pressure)
-4.17
Melting Point
77.57
pKa Acid
4.22
pKa Basic
6.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.9207
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.9207
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8595
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8595
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8418
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8418
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8011
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8011
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7910
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7910
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7795
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7795
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7648
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7648
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7562
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7562
Gibberellin receptor GID1A Q9MAA7 GID1A_ARATH Arabidopsis thaliana 3 0.7500
Gibberellin receptor GID1A Q9MAA7 GID1A_ARATH Arabidopsis thaliana 3 0.7500
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7415
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7415
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7394
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7394
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7338
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7338
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7325
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7325
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7324
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7324
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7310
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7310
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7294
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7294
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7114
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7114
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7083
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7083
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7036
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7036

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