7-deoxy-trans-dihydronarciclasine

ID: ALA251056

Chembl Id: CHEMBL251056

PubChem CID: 454239

Max Phase: Preclinical

Molecular Formula: C14H15NO6

Molecular Weight: 293.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1N[C@H]2[C@H](O)[C@H](O)[C@@H](O)C[C@@H]2c2cc3c(cc21)OCO3

Standard InChI:  InChI=1S/C14H15NO6/c16-8-1-6-5-2-9-10(21-4-20-9)3-7(5)14(19)15-11(6)13(18)12(8)17/h2-3,6,8,11-13,16-18H,1,4H2,(H,15,19)/t6-,8+,11-,12-,13+/m1/s1

Standard InChI Key:  KKAHUDOWKGIGAA-IAWGOJCDSA-N

Alternative Forms

1. Parent:

   

   ALA251056

   (2S,3R,4S,4aR,11bR)-2,3,4-trihydroxy-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

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

Calculated Properties

Molecular Weight: 293.27

Molecular Weight (Monoisotopic): 293.0899

AlogP: -0.90

#Rotatable Bonds: ┄

Polar Surface Area: 108.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.97

CX Basic pKa: ┄

CX LogP: -1.23

CX LogD: -1.23

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.49

Np Likeness Score: 1.89

References

1. Wang YH, Zhang ZK, Yang FM, Sun QY, He HP, Di YT, Mu SZ, Lu Y, Chang Y, Zheng QT, Ding M, Dong JH, Hao XJ..  (2007)  Benzylphenethylamine alkaloids from Hosta plantaginea with inhibitory activity against tobacco mosaic virus and acetylcholinesterase.,  70  (9): [PMID:17822295] [10.1021/np0702077]

2. Pettit GR, Eastham SA, Melody N, Orr B, Herald DL, McGregor J, Knight JC, Doubek DL, Pettit GR, Garner LC, Bell JA..  (2006)  Isolation and structural modification of 7-deoxynarciclasine and 7-deoxy-trans-dihydronarciclasine.,  69  (1): [PMID:16441059] [10.1021/np058068l]

3. Pettit GR, Melody N..  (2005)  Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1(1).,  68  (2): [PMID:15730244] [10.1021/np0304518]

4. Pettit GR, Pettit GR, Backhaus RA, Boyd MR, Meerow AW..  (1993)  Antineoplastic agents, 256. Cell growth inhibitory isocarbostyrils from Hymenocallis.,  56  (10): [PMID:8277308] [10.1021/np50100a004]

5. Gabrielsen B, Monath TP, Huggins JW, Kefauver DF, Pettit GR, Groszek G, Hollingshead M, Kirsi JJ, Shannon WM, Schubert EM..  (1992)  Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.,  55  (11): [PMID:1336040] [10.1021/np50089a003]

6. Chen DZ, Jiang JD, Zhang KQ, He HP, Di YT, Zhang Y, Cai JY, Wang L, Li SL, Yi P, Peng ZG, Hao XJ..  (2013)  Evaluation of anti-HCV activity and SAR study of (+)-lycoricidine through targeting of host heat-stress cognate 70 (Hsc70).,  23  (9): [PMID:23511018] [10.1016/j.bmcl.2013.02.089]

7. McNulty J, D'Aiuto L, Zhi Y, McClain L, Zepeda-Velázquez C, Ler S, Jenkins HA, Yee MB, Piazza P, Yolken RH, Kinchington PR, Nimgaonkar VL..  (2016)  iPSC Neuronal Assay Identifies Amaryllidaceae Pharmacophore with Multiple Effects against Herpesvirus Infections.,  7  (1): [PMID:26819664] [10.1021/acsmedchemlett.5b00318]

Source

Source(1):

• Scientific Literature