8alpha-O-(4-acetoxy-5-hydroxyangeloyl)-11beta,13-dihydrocnicin - Compound Card

8alpha-O-(4-acetoxy-5-hydroxyangeloyl)-11beta,13-dihydrocnicin

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8alpha-O-(4-acetoxy-5-hydroxyangeloyl)-11beta,13-dihydrocnicin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC/C(=C/COC(=O)C)/C(=O)O[C@H]1C/C(=C/CC/C(=C/[C@@H]2[C@@H]1[C@H](C)C(=O)O2)/CO)/C
InChI InChI=1S/C22H30O8/c1-13-5-4-6-16(11-23)10-19-20(14(2)21(26)29-19)18(9-13)30-22(27)17(12-24)7-8-28-15(3)25/h5,7,10,14,18-20,23-24H,4,6,8-9,11-12H2,1-3H3/b13-5+,16-10-,17-7-/t14-,18-,19+,20+/m0/s1
InChIKey QVMJTYNTCBEZMJ-UZEIXXGISA-N
Formula C22H30O8
HBA 8
HBD 2
MW 422.47
Rotatable Bonds 6
TPSA 119.36
LogP 1.61
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 422.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea pullata Asteraceae Plantae 347528

Showing of synonyms

  • Djeddi S, Karioti A, et al. (2007). Minor sesquiterpene lactones from Centaurea pullata and their antimicrobial activity. Journal of Natural Products,2007,70,1796-1799. [View] [PubMed]
Pubchem: 24178997
Nmrshiftdb2: 70021818

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C12)C=CCCC=CCC2

Level: 0

Mol. Weight: 422.47 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.740
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.460
Plasma Protein Binding
50.69
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
9.090
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.000
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.490
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.360
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
-20.510
Rat (Acute)
2.700
Rat (Chronic Oral)
2.450
Fathead Minnow
4.130
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
434.050
Hydration Free Energy
-5.300
Log(D) at pH=7.4
1.140
Log(P)
1.43
Log S
-3.37
Log(Vapor Pressure)
-8.37
Melting Point
115.22
pKa Acid
8.79
pKa Basic
4.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9506
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9506
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8811
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8811
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8473
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8473
Glycogen synthase P0A6U8 GLGA_ECOLI Escherichia coli 3 0.7872
Glycogen synthase P0A6U8 GLGA_ECOLI Escherichia coli 3 0.7872
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7399
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7399
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7240
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7240
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7058
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7058
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7046
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7046

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