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

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

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8alpha-acetoxy,13-hydroxy-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)OCC1=C2[C@@H](O)CC(=C)C(=O)CC/C(=C/[C@H]2OC1=O)/C
InChI InChI=1S/C17H20O6/c1-9-4-5-13(19)10(2)7-14(20)16-12(8-22-11(3)18)17(21)23-15(16)6-9/h6,14-15,20H,2,4-5,7-8H2,1,3H3/b9-6+/t14-,15+/m0/s1
InChIKey VPGGXYRENLSQCT-OVPGCVMQSA-N
Formula C17H20O6
HBA 6
HBD 1
MW 320.34
Rotatable Bonds 2
TPSA 89.9
LogP 1.39
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 320.13
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: 14137555
Nmrshiftdb2: 70018560

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 320.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.44
Plasma Protein Binding
41.13
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
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
7.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.69
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.53
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.97
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
-0.68
Rat (Acute)
2.63
Rat (Chronic Oral)
2.03
Fathead Minnow
4.34
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
370.56
Hydration Free Energy
-9.46
Log(D) at pH=7.4
0.93
Log(P)
0.68
Log S
-2.33
Log(Vapor Pressure)
-6.57
Melting Point
136.79
pKa Acid
7.29
pKa Basic
3.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9205
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9205
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8300
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8300
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8191
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8191
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8045
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8045
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7981
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7981
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7836
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7836
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7649
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7649
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7589
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7589
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7543
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7543
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7520
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7520
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7501
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7501
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7408
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7408
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7405
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7405
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7324
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7324
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7245
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7245
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7227
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7227
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7129
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7129

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