3-oxo-gamma-costic acid methyl ester - Compound Card

3-oxo-gamma-costic acid methyl ester

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3-oxo-gamma-costic acid methyl ester

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles COC(=O)C(=C)[C@@H]1CC[C@@]2(C(=C(C)C(=O)CC2)C1)C
InChI InChI=1S/C16H22O3/c1-10(15(18)19-4)12-5-7-16(3)8-6-14(17)11(2)13(16)9-12/h12H,1,5-9H2,2-4H3/t12-,16+/m1/s1
InChIKey BYQJMTUWCSJESL-WBMJQRKESA-N
Formula C16H22O3
HBA 3
HBD 0
MW 262.35
Rotatable Bonds 2
TPSA 43.37
LogP 3.2
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.62
Exact Mass 262.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chiliadenus montanus Asteraceae Plantae 1458965
2 Jasonia montana Asteraceae Plantae 441235
3 Crepis sancta Asteraceae Plantae —

Showing of synonyms

  • Ahmed AA, Jakupovic J, et al. (1988). 11-Hydroxyjasionone, a new sesquiterpene type from Jasonia montana. Phytochemistry,1988,27(12),3875-3877. [View]
  • Hegazy MEF, Matsuda H, et al. (2014). Chemical constituents and their antibacterial and antifungal activity from the Egyptian herbal medicine Chiliadenus montanus. Phytochemistry,2014,103,154-161. [View] [PubMed]
  • Ebada S, El-Kashef D, et al. (2019). Cytotoxic eudesmane sesquiterpenes from Crepis sancta. Phytochemistry Letters, 2019, 33, 46-48. [View] [PubMed]
Pubchem: 13819153
Nmrshiftdb2: 60067725

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C1=2)CCC(=O)C2

Level: 0

Mol. Weight: 262.35 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.51
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.460
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.86

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.680
Plasma Protein Binding
67.06
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
8.980
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.300
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.090
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.020
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
0.880
Rat (Acute)
2.330
Rat (Chronic Oral)
2.140
Fathead Minnow
4.090
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
316.350
Hydration Free Energy
-4.150
Log(D) at pH=7.4
2.710
Log(P)
2.99
Log S
-3.71
Log(Vapor Pressure)
-4.39
Melting Point
74.11
pKa Acid
11.04
pKa Basic
5.62
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7907
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7907
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7829
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7829
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7769
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7769
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7645
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7645
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7476
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7476
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7434
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7434
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7308
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7308
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7163
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7163
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7093
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7093
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7018
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7018
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7003
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7003
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7003
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7003

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