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Desacetoxymatricarin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | C[C@@H]1C(=O)O[C@H]2[C@H]1CCC(=C1[C@@H]2C(=CC1=O)C)C |
|---|---|
| InChI | InChI=1S/C15H18O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,9-10,13-14H,4-5H2,1-3H3/t9-,10-,13-,14-/m0/s1 |
| InChIKey | BJPSSVHNEGMBDQ-NUZBWSBOSA-N |
| Formula | C15H18O3 |
| HBA | 3 |
| HBD | 0 |
| MW | 246.31 |
| Rotatable Bonds | 0 |
| TPSA | 43.37 |
| LogP | 2.42 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 246.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Anthemis pseudocotula | Asteraceae | Plantae | 158231 |
| 2 | Achillea santolina | Asteraceae | Plantae | 1028379 |
| 3 | Artemisia reptans | Asteraceae | Plantae | 72350 |
Showing of synonyms
Desacetoxymatricarin
Leucodin
Leucomisine
Deacetoxymatricarin
Leukomisin
Axillin
Leukodin
Leukodin, (+)-
Desacetoxymatricarine
(+)-Leukodin
Matricarin, deacetoxy-
(3s,3as,9as,9bs)-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
UNII-1G2W00IRUI
1G2W00IRUI
DESACETOXYMATRICARIN [MI]
DTXSID20170810
11,13-DIHYDRO-DEHYDROLEUCODINE
Guaia-1(10),3-dien-12-oic acid, 6-alpha-hydroxy-2-oxo-, gamma-lactone, (11S)-
Azuleno(4,5-b)furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-3,6,9-trimethyl-, (3S,3aS,9aS,9bS)-
Azuleno(4,5-b)furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-3,6,9-trimethyl-, (3S-(3alpha,3aalpha,9aalpha,9bbeta))-
Azuleno(4,5-b)furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-3,6,9-trimethyl-,(3S,3aS,9aS,9bS)-
(3S,3aS,9aS,9bS)-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno(4,5-b)furan-2,7-dione
DTXCID9093301
17946-87-1
Leucodine
CHEBI:4441
Deacetoxy matricarin
Oligvon
SMR000445670
(3aS,9aS,9bS)-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
Spectrum_001968
SpecPlus_000876
Prestwick0_001084
Prestwick1_001084
Prestwick2_001084
Prestwick3_001084
Spectrum2_001657
Spectrum3_001631
Spectrum4_001825
Spectrum5_000589
BSPBio_001128
BSPBio_003321
KBioGR_002495
KBioSS_002530
MLS000728557
MLS002154146
DivK1c_006972
SPBio_001813
SPBio_003024
BPBio1_001242
CHEMBL517040
KBio1_001916
KBio2_002522
KBio2_005090
KBio2_007658
KBio3_002541
BJPSSVHNEGMBDQ-NUZBWSBOSA-N
HMS1571I10
HMS2098I10
HMS2221B10
BBL036667
CCG-38769
STL559046
AKOS015969701
FD69738
NCGC00163587-02
NCGC00163587-03
DA-64926
FL180377
HY-126156
AB00514036
CS-0092445
NS00094647
C09394
G90881
BRD-K96119599-001-05-4
Q27106383
Hydrate
(3S,3aR,4S,9aS,9bR)-4-hydroxy-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
Austricine
- Balboul BAAA, Ahmed AA, et al. (1997). A guaianolide and a germacranolide from Achillea santolina.. Phytochemistry,1997,46(6),1045-1049. [View]
- El-Ela MA, Jakupovic J, et al. (1990). Seco-germacranolides from Anthemis pseudocotula.. Phytochemistry,1990, 29(8),2704-2706. [View]
- Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones and acetylenes from Artemisia reptans.. Phytochemistry,1994,37(4),1055-1099. [View]
Pubchem:
167683
Cas:
17946-87-1
Gnps:
CCMSLIB00004693792
Zinc:
ZINC000005534507
Kegg Ligand:
C09394
Chebi:
4441
Nmrshiftdb2:
60058462
Chembl:
CHEMBL517040
Comptox:
DTXSID20170810
CPRiL:
234908
SMILES: O=C1C=CC(C1=2)C3C(CC(=O)O3)CCC2
Level: 0
Mol. Weight: 246.31 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.72
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.32
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.42
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.55
- Plasma Protein Binding
- 49.25
- 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
- 9.31
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.52
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.45
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.53
- 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
- 1.61
- Rat (Acute)
- 2.54
- Rat (Chronic Oral)
- 1.97
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 340.24
- Hydration Free Energy
- -5.76
- Log(D) at pH=7.4
- 1.6
- Log(P)
- 2.05
- Log S
- -2.47
- Log(Vapor Pressure)
- -5.1
- Melting Point
- 141.6
- pKa Acid
- 9.61
- pKa Basic
- 5.91
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7854 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7854 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7152 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7152 |