Zaluzanin C - Compound Card

Zaluzanin C

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Zaluzanin C

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O[C@H]1C[C@@H]2[C@H](C1=C)[C@H]1OC(=O)C(=C)[C@@H]1CCC2=C
InChI InChI=1S/C15H18O3/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h10-14,16H,1-6H2/t10-,11-,12-,13-,14-/m0/s1
InChIKey XFVLNEYIZGZDHP-PEDHHIEDSA-N
Formula C15H18O3
HBA 3
HBD 1
MW 246.31
Rotatable Bonds 0
TPSA 46.53
LogP 1.99
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 246.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cynara sibthorpiana Asteraceae Plantae 935151
2 Cheirolophus sempervirens Asteraceae Plantae 65000
3 Cheirolophus x hortigenus Asteraceae Plantae 41544

Showing of synonyms

  • Omar A, Sarg TA, et al. (1984). Guaianolides from Cynara sibthorpiana. Phytochemistry,1984,23(10),2381-2382. [View]
  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
Pubchem: 72646
Kegg Ligand: C09606
Chebi: 10103
Nmrshiftdb2: 70129178
Metabolights: MTBLC10103
CPRiL: 117435
Structure

SMILES: O=C(O1)C(=C)C(C1C23)CCC(=C)C3CCC2=C

Level: 0

Mol. Weight: 246.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.32
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.61
Plasma Protein Binding
51.38
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
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
10.05
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.12
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.44
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.83
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.91
Rat (Acute)
2.74
Rat (Chronic Oral)
1.83
Fathead Minnow
3.92
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
334.75
Hydration Free Energy
-6.02
Log(D) at pH=7.4
1.5
Log(P)
1.77
Log S
-2.67
Log(Vapor Pressure)
-5.54
Melting Point
143.82
pKa Acid
8.48
pKa Basic
6.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7676
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7676
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7648
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7648
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7396
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7396
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7248
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7248
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7242
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7242
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7231
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7231
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7118
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7118
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7021
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7021

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