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ID: ALA299161
Max Phase: Preclinical
Molecular Formula: C20H23NO2
Molecular Weight: 309.41
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCCN1Cc2ccccc2[C@@H]2c3cc(O)c(O)cc3CC[C@H]21
Standard InChI: InChI=1S/C20H23NO2/c1-2-9-21-12-14-5-3-4-6-15(14)20-16-11-19(23)18(22)10-13(16)7-8-17(20)21/h3-6,10-11,17,20,22-23H,2,7-9,12H2,1H3/t17-,20-/m1/s1
Standard InChI Key: VNVHTKVGILYCGH-YLJYHZDGSA-N
Associated Targets(non-human)
Drd1 Dopamine D1 receptor (1900 Activities)
Drd2 Dopamine D2 receptor (7893 Activities)
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Rattus norvegicus (775804 Activities)
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Adcy5 Adenylate cyclase type V (89 Activities)
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Drd1 Dopamine receptors; D1 & D2 (258 Activities)
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Molecule Features
| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 309.41 | Molecular Weight (Monoisotopic): 309.1729 | AlogP: 3.77 | #Rotatable Bonds: 2 |
| Polar Surface Area: 43.70 | Molecular Species: NEUTRAL | HBA: 3 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 3 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 9.55 | CX Basic pKa: 8.22 | CX LogP: 4.08 | CX LogD: 3.36 |
| Aromatic Rings: 2 | Heavy Atoms: 23 | QED Weighted: 0.83 | Np Likeness Score: 0.54 |
References
| 1. Brewster WK, Nichols DE, Riggs RM, Mottola DM, Lovenberg TW, Lewis MH, Mailman RB.. (1990) trans-10,11-dihydroxy-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthridine: a highly potent selective dopamine D1 full agonist., 33 (6): [PMID:1971308] [10.1021/jm00168a034] |
| 2. Mottola DM, Laiter S, Watts VJ, Tropsha A, Wyrick SD, Nichols DE, Mailman RB.. (1996) Conformational analysis of D1 dopamine receptor agonists: pharmacophore assessment and receptor mapping., 39 (1): [PMID:8568818] [10.1021/jm9502100] |
| 3. Knoerzer TA, Watts VJ, Nichols DE, Mailman RB.. (1995) Synthesis and biological evaluation of a series of substituted benzo[a]phenanthridines as agonists at D1 and D2 dopamine receptors., 38 (16): [PMID:7636869] [10.1021/jm00016a009] |
Source
Source(1):