8-epi-xanthatin-1beta,5beta-epoxide - Compound Card

8-epi-xanthatin-1beta,5beta-epoxide

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8-epi-xanthatin-1beta,5beta-epoxide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)/C=C/[C@]12O[C@@H]2C[C@H]2[C@@H](C[C@@H]1C)OC(=O)C2=C
InChI InChI=1S/C15H18O4/c1-8-6-12-11(10(3)14(17)18-12)7-13-15(8,19-13)5-4-9(2)16/h4-5,8,11-13H,3,6-7H2,1-2H3/b5-4+/t8-,11+,12+,13+,15-/m0/s1
InChIKey NGAVJIMZMAIVPV-ODTBHIJQSA-N
Formula C15H18O4
HBA 4
HBD 0
MW 262.31
Rotatable Bonds 2
TPSA 55.9
LogP 1.8
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 262.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dittrichia graveolens Asteraceae Plantae 1532790
2 Xanthium pungens Asteraceae Plantae 1979456

Showing of synonyms

  • Abou-Douh AM (2008). New eudesmane derivatives and other sesquiterpenes from the epigeal parts of Dittrichia graveolens. Chemical and Pharmaceutical Bulletin,2008,56(11),1535-1545. [View] [PubMed]
  • Ahmed AA, Jakupovic J, et al. (1990). Sesquiterpene lactones from Xanthium pungens. Phytochemistry,1990,29(7),2211-2215. [View]
Pubchem: 14633043
Nmrshiftdb2: 60077460
Bindingdb: 233134

No compound-protein relationship available.

Structure

SMILES: O=C(O1)C(=C)C(C2)C1CCC(O3)C23

Level: 0

Mol. Weight: 262.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.07
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.15
Plasma Protein Binding
23.89
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.48
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.82
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.33
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.4
Micronucleos
Toxic
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
1.85
Rat (Acute)
2.55
Rat (Chronic Oral)
1.73
Fathead Minnow
3.98
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
346.97
Hydration Free Energy
-5.52
Log(D) at pH=7.4
1.23
Log(P)
0.55
Log S
-2.41
Log(Vapor Pressure)
-5.02
Melting Point
92.19
pKa Acid
6.47
pKa Basic
5.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8947
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8947
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8499
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8499
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8266
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8266
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7665
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7665
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7537
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7537
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7332
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7332
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7300
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7300
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7221
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7221
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7211
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7211
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7176
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7176
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7053
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7053
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7034
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7034

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