Desacetyl xanthiuminol - Compound Card

Desacetyl xanthiuminol

Select a section from the left sidebar

Desacetyl xanthiuminol

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(CC(C1=CC[C@H]2[C@H](C[C@@H]1C)OC(=O)C2=C)O)O
InChI InChI=1S/C15H22O4/c1-8-6-14-12(10(3)15(18)19-14)5-4-11(8)13(17)7-9(2)16/h4,8-9,12-14,16-17H,3,5-7H2,1-2H3/t8-,9?,12+,13?,14-/m0/s1
InChIKey TVKYSIIBPQZNFW-DBPPGLDUSA-N
Formula C15H22O4
HBA 4
HBD 2
MW 266.34
Rotatable Bonds 3
TPSA 66.76
LogP 1.57
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 266.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Xanthium spinosum Asteraceae Plantae 1053410

Showing of synonyms

  • Omar AA, Elrashidy EM, et al. (1984). Xanthanolides from Xanthium spinosum. Phytochemistry,1984,23(4),915-916. [View]
Pubchem: 162970311
Nmrshiftdb2: 60063645

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 266.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.98
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.29
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.47
Plasma Protein Binding
35.79
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
7.14
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.08
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.95
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.7
Micronucleos
Safe
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
1.09
Rat (Acute)
3.02
Rat (Chronic Oral)
1.96
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
341.19
Hydration Free Energy
-9.96
Log(D) at pH=7.4
0.84
Log(P)
0.31
Log S
-1.95
Log(Vapor Pressure)
-6.1
Melting Point
101.22
pKa Acid
9.21
pKa Basic
5.84
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 0.9379
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9379
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9328
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9328
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9169
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9169
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9091
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9091
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8961
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8961
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8733
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8733
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8362
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8362
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8259
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8259
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8154
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8154
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8082
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8082
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7959
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7959
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7919
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7919
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7874
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7874
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7859
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7859
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7817
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7817
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 4 0.7732
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 4 0.7732
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7689
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7689
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7683
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7683
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7632
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7632
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7395
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7395
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7388
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7388
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7372
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7372
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7280
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7280
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7228
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7228
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7211
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7211
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7210
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7210
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7202
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7202
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7194
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7194
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7081
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7081
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7045
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7045

Download SDF