Inuloxin B - Compound Card

Inuloxin B

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Inuloxin B

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C[C@@H]1CCC(=O)/C(=C/C[C@H]2[C@@H](C1)OC(=O)[C@H]2C)/C
InChI InChI=1S/C15H22O3/c1-9-4-7-13(16)10(2)5-6-12-11(3)15(17)18-14(12)8-9/h5,9,11-12,14H,4,6-8H2,1-3H3/b10-5+/t9-,11+,12-,14-/m1/s1
InChIKey YUOIZQYKJGLEKZ-JDNCVLFSSA-N
Formula C15H22O3
HBA 3
HBD 0
MW 250.34
Rotatable Bonds 0
TPSA 43.37
LogP 2.89
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 250.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Inula viscosa Asteraceae Plantae 56525

Showing of synonyms

  • Andolfi A, Zermane N, et al. (2013). Inuloxins A-D, phytotoxic bi-and tri-cyclic sesquiterpene lactones produced by Inula viscosa: potential for broomrapes and field dodder management. Phytochemistry,2013,86,112-120. [View]
Pubchem: 102194604

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C12)CCCCC(=O)C=CC2

Level: 0

Mol. Weight: 250.34 g/mol

Phytotoxicity

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
48.84
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
10.32
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.18
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.78
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.24
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.42
Rat (Acute)
1.91
Rat (Chronic Oral)
1.8
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
327.15
Hydration Free Energy
-5.14
Log(D) at pH=7.4
2.17
Log(P)
2.02
Log S
-2.97
Log(Vapor Pressure)
-4.32
Melting Point
84.95
pKa Acid
10.41
pKa Basic
5.25
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.8082
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.8082
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8034
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8034
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7834
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7834
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7738
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7738
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7394
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7394
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7383
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7383
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7302
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7302
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7234
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7234
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7230
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7230
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7178
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7178
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7083
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7083
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7041
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7041
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7019
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7019
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7004
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7004

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