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Damsin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | C[C@H]1CC[C@@H]2[C@H]([C@]3([C@H]1CCC3=O)C)OC(=O)C2=C |
|---|---|
| InChI | InChI=1S/C15H20O3/c1-8-4-5-10-9(2)14(17)18-13(10)15(3)11(8)6-7-12(15)16/h8,10-11,13H,2,4-7H2,1,3H3/t8-,10-,11-,13+,15-/m0/s1 |
| InChIKey | HPJYKMSFRBJOSW-JHSUYXJUSA-N |
| Formula | C15H20O3 |
| HBA | 3 |
| HBD | 0 |
| MW | 248.32 |
| Rotatable Bonds | 0 |
| TPSA | 43.37 |
| LogP | 2.5 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.73 |
| Exact Mass | 248.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ambrosia maritima | Asteraceae | Plantae | 1028380 |
| 2 | Ambrosia maritima | Asteraceae | Plantae | 1028380 |
Showing of synonyms
Damsin
Ambrosin, dihydro-
Dihydroambrosin
1216-42-8
(3aS,6S,6aS,9aR,9bR)-6,9a-dimethyl-3-methylidene-3a,4,5,6,6a,7,8,9b-octahydroazuleno[8,7-b]furan-2,9-dione
NSC 85249
Decahydro-6,9a-dimethyl-3-methylene-azuleneo(4,5-b)furan-2,9-dione
10alphaH-Ambros-11(13)-en-12-oic acid, 6beta-hydroxy-4-oxo-, gamma-lactone
10-alpha-H-AMBROS-11(13)-EN-12-OIC ACID, 6-beta-HYDROXY-4-OXO-, gamma-LACTONE
Azuleno(4,5-b)furan-2,9-dione, decahydro-6,9a-dimethyl-3-methylene-, (3aS-(3aalpha,6beta,6aalpha,9abeta,9balpha))-
(3aS,6S,6aS,9aR,9bR)-6,9a-dimethyl-3-methylidene-3a,4,5,6,6a,7,8,9b-octahydroazuleno(8,7-b)furan-2,9-dione
(3aS,6S,6aS,9aR,9bR)-6,9a-dimethyl-3-methylene-3a,4,5,6,6a,7,8,9b-octahydroazuleno(8,7-b)furan-2,9-dione
(3aS,6S,6aS,9aR,9bR)-6,9a-dimethyl-3-methylene-3a,4,5,6,6a,7,8,9b-octahydroazuleno[8,7-b]furan-2,9-dione
10alphaH-Ambros-11(13)-en-12-oic acid, 6beta-hydroxy-4-oxo-, gamma-lactone (8CI)
Azuleno(4,5-b)furan-2,9-dione, decahydro-6,9a-dimethyl-3-methylene-, (3aS-(3aalpha,6beta,6aalpha,9abeta,9balpha))-(9CI)
Damsine
CHEBI:4314
NSC85249
Azulene derivative
CHEMBL2286469
SCHEMBL18642932
DTXSID70923878
NSC-85249
NS00094027
C09386
Q27106332
10.alpha.H-Ambros-11(13)-en-12-oic acid, .gamma.-lactone
6,9a-Dimethyl-3-methylidenedecahydroazuleno[4,5-b]furan-2,9-dione
Azuleno[4,9-dione, decahydro-6,9a-dimethyl-3-methylene-, [3aS-(3a.alpha.,6.beta.,6a.alpha.,9a.beta.,9b.alpha.)]-
- Saad MMG, Abdelgaleil SAM, et al. (2012). Herbicidal potential of pseudoguaninolide sesquiterpenes on wild oat, Avena fatua L.. Biochemical Systematics and Ecology,2012,44,333-337. [View]
- Picman AK, Arnason JT, et al. (1986). Hymenin, another sesquiterpene lactone in Ambrosia maritima.. Journal of Natural Products,1986,49(3),556-556. [View]
No compound-protein relationship available.
SMILES: O=C(O1)C(=C)C(C1C23)CCCC3CCC2=O
Level: 0
Mol. Weight: 248.32 g/mol
Phytotoxicity
Absorption
- Caco-2 (logPapp)
- -4.64
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.57
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.08
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.63
- Plasma Protein Binding
- 49.47
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- 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
- 13.38
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.13
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.08
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.94
- Micronucleos
- Safe
- 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
- 0.69
- Rat (Acute)
- 2.21
- Rat (Chronic Oral)
- 1.55
- 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
- 330.85
- Hydration Free Energy
- -5.1
- Log(D) at pH=7.4
- 1.72
- Log(P)
- 1.88
- Log S
- -2.93
- Log(Vapor Pressure)
- -4.45
- Melting Point
- 142.15
- pKa Acid
- 9.71
- pKa Basic
- 5.69
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.9059 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.9059 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8115 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8115 |