4,5-dioxo-11betaH-xanth-1(10)-en-12,8beta-olide - Compound Card

4,5-dioxo-11betaH-xanth-1(10)-en-12,8beta-olide

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4,5-dioxo-11betaH-xanth-1(10)-en-12,8beta-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)CCC1=C(C)C[C@@H]2[C@H](CC1=O)[C@H](C(=O)O2)C
InChI InChI=1S/C15H20O4/c1-8-6-14-12(10(3)15(18)19-14)7-13(17)11(8)5-4-9(2)16/h10,12,14H,4-7H2,1-3H3/t10-,12-,14-/m1/s1
InChIKey UUKUKOWRPZPCIE-MPKXVKKWSA-N
Formula C15H20O4
HBA 4
HBD 0
MW 264.32
Rotatable Bonds 3
TPSA 60.44
LogP 2.21
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dittrichia graveolens Asteraceae Plantae 1532790

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]
Pubchem: 10706730
Nmrshiftdb2: 70037140

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C12)CC=CC(=O)C2

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.58
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.62
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.53
Plasma Protein Binding
52.28
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
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
9.37
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.25
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.59
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.49
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
1.15
Rat (Acute)
2.51
Rat (Chronic Oral)
1.9
Fathead Minnow
3.91
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
339.2
Hydration Free Energy
-7.32
Log(D) at pH=7.4
0.73
Log(P)
0.82
Log S
-2.01
Log(Vapor Pressure)
-5.51
Melting Point
107.78
pKa Acid
9.84
pKa Basic
3.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9646
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9646
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8983
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8983
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8843
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8843
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8413
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8413
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8374
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8374
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8284
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8284
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8203
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8203
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8133
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8133
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8015
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8015
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7912
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7912
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7844
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7844
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7840
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7840
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7588
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7588
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7562
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7562
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7428
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7428
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7401
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7401
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7310
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7310
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7280
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7280
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7278
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7278
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7251
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7251
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7193
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7193
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7186
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7186
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7182
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7182
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7170
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7170
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7127
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7127
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7088
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7088
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7069
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7069
Cytidine deaminase P19079 CDD_BACSU Bacillus subtilis 3 0.7027
Cytidine deaminase P19079 CDD_BACSU Bacillus subtilis 3 0.7027

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