3alpha-acetyl-gamma-costic acid - Compound Card

3alpha-acetyl-gamma-costic acid

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3alpha-acetyl-gamma-costic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Derivative
Canonical Smiles CC(=O)O[C@@H]1CC[C@]2(C(=C1C)C[C@@H](CC2)C(=C)C(=O)O)C
InChI InChI=1S/C17H24O4/c1-10(16(19)20)13-5-7-17(4)8-6-15(21-12(3)18)11(2)14(17)9-13/h13,15H,1,5-9H2,2-4H3,(H,19,20)/t13-,15-,17+/m1/s1
InChIKey BXNPZLISNVPPDU-UNEWFSDZSA-N
Formula C17H24O4
HBA 3
HBD 1
MW 292.38
Rotatable Bonds 3
TPSA 63.6
LogP 3.48
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 292.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chiliadenus montanus Asteraceae Plantae 1458965

Showing of synonyms

  • 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]
Pubchem: 162816978
Nmrshiftdb2: 70083418

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C1=2)CCCC2

Level: 0

Mol. Weight: 292.38 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.64
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.62
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.51

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.64
Plasma Protein Binding
59.85
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
4.51
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.28
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.11
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.46
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
-1.0
Rat (Acute)
2.34
Rat (Chronic Oral)
2.43
Fathead Minnow
3.93
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
339.9
Hydration Free Energy
-5.97
Log(D) at pH=7.4
0.64
Log(P)
3.84
Log S
-3.67
Log(Vapor Pressure)
-5.94
Melting Point
129.99
pKa Acid
4.99
pKa Basic
7.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8934
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8934
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8920
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8920
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8780
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8780
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8685
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8685
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8560
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8560
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8535
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8535
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8221
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8221
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8078
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8078
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8020
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8020
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7979
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7979
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7856
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7856
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7737
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7737
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7666
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7666
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7664
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7664
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7638
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7638
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7591
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7591
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7556
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7556
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7503
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7503
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7410
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7410
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7349
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7349
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7207
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7207
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7039
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7039

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