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Parthenin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | O=C1O[C@@H]2[C@H](C1=C)CC[C@@H]([C@]1([C@@]2(C)C(=O)C=C1)O)C |
|---|---|
| InChI | InChI=1S/C15H18O4/c1-8-4-5-10-9(2)13(17)19-12(10)14(3)11(16)6-7-15(8,14)18/h6-8,10,12,18H,2,4-5H2,1,3H3/t8-,10-,12+,14-,15+/m0/s1 |
| InChIKey | LLQCRTZROWMVOL-JISBIHODSA-N |
| Formula | C15H18O4 |
| HBA | 4 |
| HBD | 1 |
| MW | 262.31 |
| Rotatable Bonds | 0 |
| TPSA | 63.6 |
| LogP | 1.39 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 262.12 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ambrosia maritima | Asteraceae | Plantae | 1028380 |
| 2 | Dichrocephala integrifolia | Asteraceae | Plantae | 1573921 |
Showing of synonyms
Parthenin
508-59-8
UNII-982DJP4W6A
982DJP4W6A
NSC 85239
PARTHENIN [MI]
DTXSID40877834
NSC-85239
(3aS,6S,6aS,9aS,9bR)-6a-hydroxy-6,9a-dimethyl-3-methylidene-4,5,6,9b-tetrahydro-3aH-azuleno[8,7-b]furan-2,9-dione
10-alpha-H-Ambrosa-2,11(13)-dien-12-oic acid, 1,6-beta-dihydroxy-4-oxo-, gamma-lactone
10alphaH-Ambrosa-2,11(13)-dien-12-oic acid, 1,6beta-dihydroxy-4-oxo-, gamma-lactone
(3aS-(3aalpha,6beta,6aalpha,9abeta,9balpha))-3,3a,4,5,6,6a,9a,9b-Octahydro-6a-hydroxy-6,9a-dimethyl-3-methyleneazuleno (4,5-b)furan-2,9-dione
Azuleno(4,5-b)furan-2,9-dione, 3,3a,4,5,6,6a,9a,9b-octahydro-6a-hydroxy-6,9a-dimethyl-3-methylene-, (3aS-(3aalpha,6beta,6aalpha,9abeta,9balpha))-
10.alpha.H-Ambrosa-2,11(13)-dien-12-oic acid, 1,6.beta.-dihydroxy-4-oxo-, .gamma.-lactone
AZULENO(4,5-B)FURAN-2,9-DIONE, 3,3A,4,5,6,6A,9A,9B-OCTAHYDRO-6A-HYDROXY-6,9A-DIMETHYL-3-METHYLENE-, (3AS,6S,6AS,9AS,9BR)-
(3aS,6S,6aS,9aS,9bR)-6a-hydroxy-6,9a-dimethyl-3-methylidene-4,5,6,9b-tetrahydro-3aH-azuleno(8,7-b)furan-2,9-dione
Azuleno[4,5-b]furan-2,9-dione, 3,3a,4,5,6,6a,9a,9b-octahydro-6a-hydroxy-6,9a-dimethyl-3-methylene-, (3aS,6S,6aS,9aS,9bR)-
DTXCID601015901
Parthenin, 3aS-(3aalpha,6beta,6abeta,9beta,9balpha)-isomer
(3aS-(3a alpha,6 beta,6a alpha,9a beta,9b alpha))-3,3a,4,5,6,6a,9a,9b-octahydro-6a-hydroxy-6,9a-dimethyl-3-methyleneazuleno (4,5-b)furan-2,9-dione
10alphaH-Ambrosa-2,11(13)-dien-12-oic acid, 1,6beta-dihydroxy-4-oxo-, gamma-lactone (8CI)
Azuleno(4,5-b)furan-2,9-dione, 3,3a,4,5,6,6a,9a,9b-octahydro-6a-hydroxy-6,9a-dimethyl-3-methylene-, (3aS-(3aalpha,6beta,6aalpha,9abeta,9balpha))-(9CI)
Parthenicin
CHEBI:7938
Partenin
SCHEMBL382003
CHEMBL401149
LMPR0103420001
NS00094714
C09523
Q27107626
- Morikawa T, Abdel-Halim OB, et al. (2006). Pseudoguaiane-type sesquiterpenes and inhibitors on nitric oxide production from Dichrocephala integrifolia. Tetrahedron,2006,6,6435-6442. [View]
- Salam NAA, Mahmoud ZF, et al. (1984). Sesquiterpene lactones from Ambrosia maritima (Damssissa).. Phytochemistry,1984,23(12),2851-2853. [View]
Pubchem:
442288
Cas:
508-59-8
Zinc:
ZINC000003917773
Kegg Ligand:
C09523
Chebi:
7938
Nmrshiftdb2:
20028270
Chembl:
CHEMBL401149
Comptox:
DTXSID40877834
CPRiL:
80828
SMILES: C=C1C(=O)OC2C1CCCC(C23)C=CC3=O
Level: 0
Mol. Weight: 262.31 g/mol
Inhibitory on nitric oxide production
Absorption
- Caco-2 (logPapp)
- -4.7
- 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
- -2.27
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.44
- Plasma Protein Binding
- 46.54
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- 7.0
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.12
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- 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
- 4.5
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 0.89
- Rat (Acute)
- 2.74
- Rat (Chronic Oral)
- 1.74
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 328.43
- Hydration Free Energy
- -8.06
- Log(D) at pH=7.4
- 0.96
- Log(P)
- 0.91
- Log S
- -2.56
- Log(Vapor Pressure)
- -6.48
- Melting Point
- 183.57
- pKa Acid
- 7.44
- pKa Basic
- 5.24
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8698 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8698 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7478 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7478 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7162 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7162 |