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Matricarin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | CC(=O)O[C@H]1CC(=C2[C@@H]([C@@H]3[C@@H]1[C@H](C)C(=O)O3)C(=CC2=O)C)C |
|---|---|
| InChI | InChI=1S/C17H20O5/c1-7-5-11(19)13-8(2)6-12(21-10(4)18)15-9(3)17(20)22-16(15)14(7)13/h5,9,12,14-16H,6H2,1-4H3/t9-,12-,14-,15+,16+/m0/s1 |
| InChIKey | QONYNSMAVSRIRD-UPQAZBFISA-N |
| Formula | C17H20O5 |
| HBA | 5 |
| HBD | 0 |
| MW | 304.34 |
| Rotatable Bonds | 1 |
| TPSA | 69.67 |
| LogP | 1.96 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.59 |
| Exact Mass | 304.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Achillea ligustica | Asteraceae | Plantae | 282745 |
| 2 | Ambrosia maritima | Asteraceae | Plantae | 1028380 |
| 3 | Achillea santolina | Asteraceae | Plantae | 1028379 |
Showing of synonyms
Matricarin
5989-43-5
UNII-N0027B7ESK
N0027B7ESK
AUSTRICIN, ACETATE
DTXSID60208606
Azuleno(4,5-b)furan-2,7-dione, 4-(acetyloxy)-3,3a,4,5,9a,9b-hexahydro-3,6,9-trimethyl-, (3S-(3alpha,3aalpha,4alpha,9aalpha,9bbeta))-
AZULENO(4,5-B)FURAN-2,7-DIONE, 4-(ACETYLOXY)-3,3A,4,5,9A,9B-HEXAHYDRO-3,6,9-TRIMETHYL-, (3S,3AR,4S,9AS,9BR)-
DTXCID70131097
GUAIA-1(10),3-DIEN-12-OIC ACID, 6alpha,8alpha-DIHYDROXY-2-OXO-, 12,6-LACTONE, ACETATE, (11S)-
MATRICARIN [MI]
CHEMBL2087220
CHEBI:174918
AKOS015969716
Guaia-1(10),3-dien-12-oic acid, 6.alpha.,8.alpha.-dihydroxy-2-oxo-, 12,6-lactone, acetate, (11S)-
Q27284313
[(3S,3aR,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]uran-4-yl] acetate
- Balboul BAAA, Ahmed AA, et al. (1997). A guaianolide and a germacranolide from Achillea santolina.. Phytochemistry,1997,46(6),1045-1049. [View]
- Hegazy MEF, Mohamed AEHH, et al. (2014). A new chlorine-containing sesquiterpene lactone from Achillea ligustica.. Zeitschrift für Naturforschung B,2014,63(1),105-107. [View]
- Mahmoud AA, Ahmed AA, et al. (1999). A new chlorosesquiterpene lactone from Ambrosia maritima.. Fitoterapia,1999,70,575-578. [View]
Pubchem:
3083923
Cas:
5989-43-5
Zinc:
ZINC000006018862
Chebi:
174918
Nmrshiftdb2:
60058305
Chembl:
CHEMBL2087220
Comptox:
DTXSID60208606
CPRiL:
425898
SMILES: O=C1C=CC(C1=2)C3C(CC(=O)O3)CCC2
Level: 0
Mol. Weight: 304.34 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.67
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.54
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.35
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.47
- Plasma Protein Binding
- 49.67
- 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
- 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
- 11.17
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.17
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.32
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.37
- 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
- -0.16
- Rat (Acute)
- 2.71
- Rat (Chronic Oral)
- 2.04
- 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
- 362.87
- Hydration Free Energy
- -5.88
- Log(D) at pH=7.4
- 1.04
- Log(P)
- 1.2
- Log S
- -2.8
- Log(Vapor Pressure)
- -6.14
- Melting Point
- 177.16
- pKa Acid
- 9.21
- pKa Basic
- 5.08
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.9078 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.9078 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8691 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8691 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8622 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8622 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8102 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8102 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7375 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7375 |