Pungiolide B - Compound Card

Pungiolide B

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Pungiolide B

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)/C=C/C12OC2CC2C(CC1C)OC(=O)C12OC2CC3C(CC(C2(C=C1C(=O)C)O)C)OC(=O)C3=C
InChI InChI=1S/C29H34O9/c1-13-8-21-18(16(4)25(32)35-21)10-23-27(13,34)12-20(17(5)31)29(38-23)19-11-24-28(37-24,7-6-15(3)30)14(2)9-22(19)36-26(29)33/h6-7,12-14,18-19,21-24,34H,4,8-11H2,1-3,5H3/b7-6+
InChIKey SWQFFFCGVOKUSC-VOTSOKGWSA-N
Formula C29H34O9
HBA 9
HBD 1
MW 526.58
Rotatable Bonds 3
TPSA 128.73
LogP 2.15
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.66
Exact Mass 526.22
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Xanthium pungens Asteraceae Plantae 1979456

Showing of synonyms

  • Ahmed AA, Jakupovic J, et al. (1990). Sesquiterpene lactones from Xanthium pungens. Phytochemistry,1990,29(7),2211-2215. [View]
Pubchem: 5932673

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(CC2)C1CC(O3)C2C=CC34C5C(OC4=O)CCC6C(O6)C5

Level: 0

Mol. Weight: 526.58 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.05
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
20.26
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
13.74
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.13
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.04
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.3
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
-1747.79
Rat (Acute)
4.79
Rat (Chronic Oral)
2.13
Fathead Minnow
10.18
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
451.28
Hydration Free Energy
-2.85
Log(D) at pH=7.4
2.0
Log(P)
0.2
Log S
-4.6
Log(Vapor Pressure)
-8.19
Melting Point
175.04
pKa Acid
4.49
pKa Basic
2.02
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 0.8300
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8300
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8198
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8198
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7083
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7083
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7021
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7021

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