ID: ALA225230

Max Phase: Preclinical

Molecular Formula: C19H21NO2

Molecular Weight: 295.38

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCCN1CCc2cccc3c2[C@H]1Cc1ccc(O)c(O)c1-3

Standard InChI:  InChI=1S/C19H21NO2/c1-2-9-20-10-8-12-4-3-5-14-17(12)15(20)11-13-6-7-16(21)19(22)18(13)14/h3-7,15,21-22H,2,8-11H2,1H3/t15-/m1/s1

Standard InChI Key:  BTGAJCKRXPNBFI-OAHLLOKOSA-N

Molecule Features

Natural Product: Yes

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

Properties

Molecular Weight: 295.38

Molecular Weight (Monoisotopic): 295.1572

AlogP: 3.63

#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: 9.30

CX Basic pKa: 8.24

CX LogP: 3.69

CX LogD: 3.01

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.83

Np Likeness Score: 0.93

References

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2. Neumeyer JL, Arana GW, Law SJ, Lamont JS, Kula NS, Baldessarini RJ..  (1981)  Aporphines, 36. Dopamine receptor interactions of trihydroxyaporphines. Synthesis, radioreceptor binding, and striatal adenylate cyclase stimulation of 2,10,11-trihydroxyaporphines in comparison with other hydroxylated aporphines.,  24  (12): [PMID:7310821] [10.1021/jm00144a014]

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4. Gao YG, Baldessarini RJ, Kula NS, Neumeyer JL..  (1990)  Synthesis and dopamine receptor affinities of enantiomers of 2-substituted apomorphines and their N-n-propyl analogues.,  33  (6): [PMID:1971309] [10.1021/jm00168a040]

5. Neumeyer JL, Gao YG, Kula NS, Baldessarini RJ..  (1991)  R and S enantiomers of 11-hydroxy- and 10,11-dihydroxy-N-allylnoraporphine: synthesis and affinity for dopamine receptors in rat brain tissue.,  34  (1): [PMID:1671415] [10.1021/jm00105a005]

6. Wilcox RE, Huang WH, Brusniak MY, Wilcox DM, Pearlman RS, Teeter MM, DuRand CJ, Wiens BL, Neve KA..  (2000)  CoMFA-based prediction of agonist affinities at recombinant wild type versus serine to alanine point mutated D2 dopamine receptors.,  43  (16): [PMID:10956209] [10.1021/jm990526y]

7. Neumeyer JL, Gao YG, Kula NS, Baldessarini RJ..  (1990)  Synthesis and dopamine receptor affinity of (R)-(-)-2-fluoro-N-n-propylnorapomorphine: a highly potent and selective dopamine D2 agonist.,  33  (12): [PMID:2147956] [10.1021/jm00174a002]

8. Neumeyer JL, Guan JH, Niznik HB, Dumbrille-Ross A, Seeman P, Padmanabhan S, Elmaleh DR..  (1985)  Novel photoaffinity label for the dopamine D2 receptor: synthesis of 4-azido-5-iodo-2-methoxy-N-[1-(phenylmethyl)-4-piperidinyl] benzamide (iodoazidoclebopride, IAC) and the corresponding 125I-labeled analogue (125IAC).,  28  (4): [PMID:3156993] [10.1021/jm00382a002]

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11. Brusniak MY, Pearlman RS, Neve KA, Wilcox RE..  (1996)  Comparative molecular field analysis-based prediction of drug affinities at recombinant D1A dopamine receptors.,  39  (4): [PMID:8632409] [10.1021/jm950447w]

12. Neumeyer JL, Law SJ, Meldrum B, Anlezark G, Watling KJ..  (1981)  Aporphines. 34. (-)-2,10,11-Trihydroxy-N-n-propylnoraporphine, a novel dopaminergic aporphine alkaloid with anticonvulsant activity.,  24  (7): [PMID:7277402] [10.1021/jm00139a027]

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17. PubChem BioAssay data set, 

18. PubChem BioAssay data set, 

19. Sromek AW, Si YG, Zhang T, George SR, Seeman P, Neumeyer JL..  (2011)  Synthesis and Evaluation of Fluorinated Aporphines: Potential Positron Emission Tomography Ligands for D2 Receptors,  2  (3): [PMID:21666830] [10.1021/ml1001689]

20. PubChem BioAssay data set, 

21. Costall B, Naylor RJ..  (1977)  Aporphines, 21. (1,2) Dopaminergic activity of aporphine and benzylisoquinoline derivatives. Synthesis of 8-hydroxyaporphines and 1-(hydroxybenzyl)-2-n-propyl-1,2,3,4-tetrahydroisoquinolines.,  20  (2): [PMID:556776] [10.1021/jm00212a002]

22. Neumeyer JL, Reinhard JF, Dafeldecker WP, Guarino J, Kosersky DS, Fuxe K, Agnati L..  (1976)  Aporphines. 14 Dopaminergic and antinociceptive activity of aporphine derivatives. Synthesis of 10-hydroxyaporphines and 10-hydroxy-N-n-propylnoraporphine.,  19  (1): [PMID:942751] [10.1021/jm00223a006]

23. Park H, Urs AN, Zimmerman J, Liu C, Wang Q, Urs NM..  (2020)  Structure-Functional-Selectivity Relationship Studies of Novel Apomorphine Analogs to Develop D1R/D2R Biased Ligands.,  11  (3): [PMID:32184974] [10.1021/acsmedchemlett.9b00575]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays