8alpha,13-diacetoxy-1-oxo-germacra-4,7(11),10(14)-trien-6alpha,12-olide - Compound Card

8alpha,13-diacetoxy-1-oxo-germacra-4,7(11),10(14)-trien-6alpha,12-olide

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8alpha,13-diacetoxy-1-oxo-germacra-4,7(11),10(14)-trien-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@H]1CC(=C)C(=O)CC/C(=C/[C@@H]2C1=C(COC(=O)C)C(=O)O2)/C
InChI InChI=1S/C19H22O7/c1-10-5-6-15(22)11(2)8-17(25-13(4)21)18-14(9-24-12(3)20)19(23)26-16(18)7-10/h7,16-17H,2,5-6,8-9H2,1,3-4H3/b10-7+/t16-,17+/m1/s1
InChIKey TXDXTWAWXLMXOQ-CFMJQPPZSA-N
Formula C19H22O7
HBA 7
HBD 0
MW 362.38
Rotatable Bonds 3
TPSA 95.97
LogP 1.96
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 362.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Brocchia cinerea Asteraceae Plantae 282208
2 Cotula cinerea Asteraceae Plantae —

Showing of synonyms

  • Jakupovic J, Aal MA, et al. (1988). Further glaucolides and other sesquiterpene lactones from Brocchia cinerea.. Phytochemistry,1988,27(7),2219-2224. [View]
  • Metwally MA, El-dahmy S, et al. (1986). Glaucolide-like sesquiterpene lactones from Cotula cinerea. Phytochemistry,1986,25(1),255-257. [View]
Pubchem: 14137557
Nmrshiftdb2: 70018556

No compound-protein relationship available.

Structure

SMILES: C1CC(=C)C(=O)CCC=CC(C1=2)OC(=O)C2

Level: 0

Mol. Weight: 362.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.62
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.37
Plasma Protein Binding
50.56
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
9.52
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.19
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.11
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.65
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1.77
Rat (Acute)
2.16
Rat (Chronic Oral)
2.24
Fathead Minnow
4.52
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
381.28
Hydration Free Energy
-7.47
Log(D) at pH=7.4
1.58
Log(P)
0.93
Log S
-3.0
Log(Vapor Pressure)
-6.66
Melting Point
127.9
pKa Acid
8.22
pKa Basic
3.89
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8058
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8058
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7879
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7879
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7833
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7833
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7385
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7385
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7271
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7271
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7248
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7248
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7125
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7125
Cytidine deaminase P19079 CDD_BACSU Bacillus subtilis 3 0.7041
Cytidine deaminase P19079 CDD_BACSU Bacillus subtilis 3 0.7041

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