3-oxo-eudesma-4,11(13)-dien-12-oic acid - Compound Card

3-oxo-eudesma-4,11(13)-dien-12-oic acid

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3-oxo-eudesma-4,11(13)-dien-12-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OC(=O)C(=C)[C@@H]1CC[C@@]2(C(=C(C)C(=O)CC2)C1)C
InChI InChI=1S/C15H20O3/c1-9(14(17)18)11-4-6-15(3)7-5-13(16)10(2)12(15)8-11/h11H,1,4-8H2,2-3H3,(H,17,18)/t11-,15+/m1/s1
InChIKey RDGFGQJFNSCICW-ABAIWWIYSA-N
Formula C15H20O3
HBA 2
HBD 1
MW 248.32
Rotatable Bonds 2
TPSA 54.37
LogP 3.11
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 248.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329
2 Achillea fragrantissima Asteraceae Plantae 282738
3 Chiliadenus montanus Asteraceae Plantae 1458965
4 Jasonia montana Asteraceae Plantae 441235
5 Tarchonanthus camphoratus Asteraceae Plantae 41650
6 Xanthium pungens Asteraceae Plantae 1979456

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]
  • Ahmed AA, Abou-El-Ela M, et al. (1990). Eudesmanolides and other constituents from Artemisia herba-alba.. Phytochemistry,1990,29(11),3661-3663. [View]
  • Ahmed AA, Jakupovk J, et al. (1990). Irregular oxygenated monoterpenes from Achillea fragrantissima.. Phytochemistry,1990,29(4),1322-1324. [View]
  • Hegazy MEF, Tawfik WA, et al. (2015). Sesquiterpene acid derivatives from Tarchonanthus camphoratus. Research Journal of Pharmaceutical, Biological and Chemical Sciences,2015,6(1),659-663. [View]
  • Ahmed AA, Jakupovic J, et al. (1990). Sesquiterpene lactones from Xanthium pungens. Phytochemistry,1990,29(7),2211-2215. [View]
Pubchem: 11054003
Nmrshiftdb2: 60067719

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 248.32 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.55
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.64
Plasma Protein Binding
64.12
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
5.02
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.48
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.39
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.93
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
0.44
Rat (Acute)
2.21
Rat (Chronic Oral)
2.41
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
327.42
Hydration Free Energy
-7.25
Log(D) at pH=7.4
0.15
Log(P)
2.39
Log S
-3.05
Log(Vapor Pressure)
-5.56
Melting Point
141.1
pKa Acid
4.8
pKa Basic
8.0
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7978
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7978
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7739
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7739
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7624
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7624
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7536
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7536
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7404
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7404
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7380
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7380
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7299
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7299
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7039
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7039

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