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C19H22N2O2
APtclcactv08052300402D 0   0.00000     0.00000
 
 45 49  0  0  1  0  0  0  0  0999 V2000
    3.8021    0.0794    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7040   -1.5458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6458    1.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5764    1.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1319    2.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903    2.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1285   -2.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1248   -2.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -1.4245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1803    0.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8137   -0.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4950   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6523   -1.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1213   -1.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6509   -2.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6264   -2.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8090   -0.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3781   -0.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1111    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1111    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4201    0.0794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8706   -1.1716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6111   -0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2663    0.7393    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706    0.5915    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1940   -0.0468    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7682   -1.9211    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0901   -1.1906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3029   -2.4890    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0972   -2.4086    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7289   -1.4286    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6072   -2.2553    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2657    1.9173    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9565    1.9173    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7334   -3.2101    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -2.5699    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5299   -2.6130    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1837   -3.0688    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576   -3.0773    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8198   -3.4196    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0720   -3.1541    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7426   -2.5892    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1776   -1.9186    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4440    3.3662    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7782    3.3662    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 23  1  0  0  0  0
 22 23  1  0  0  0  0
  1 23  1  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
  1 20  1  0  0  0  0
 18 21  1  0  0  0  0
  1 11  1  0  0  0  0
  2 23  1  0  0  0  0
  9 17  2  0  0  0  0
 12 18  1  0  0  0  0
 10 18  2  0  0  0  0
  2 13  1  0  0  0  0
 14 22  1  0  0  0  0
  3 19  1  0  0  0  0
  4 20  1  0  0  0  0
  2 15  1  0  0  0  0
  2  7  1  6  0  0  0
 14 16  1  0  0  0  0
  7  8  1  0  0  0  0
  3  5  2  0  0  0  0
  4  6  2  0  0  0  0
  1 24  1  6  0  0  0
 11 17  1  0  0  0  0
 19 20  2  0  0  0  0
 12 13  1  0  0  0  0
 15 16  1  0  0  0  0
  5  6  1  0  0  0  0
 11 25  1  0  0  0  0
 11 26  1  0  0  0  0
 12 27  1  0  0  0  0
 12 28  1  0  0  0  0
 13 29  1  0  0  0  0
 13 30  1  0  0  0  0
 14 31  1  0  0  0  0
 14 32  1  0  0  0  0
  3 33  1  0  0  0  0
  4 34  1  0  0  0  0
 15 35  1  0  0  0  0
 15 36  1  0  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
 16 39  1  0  0  0  0
 16 40  1  0  0  0  0
  8 41  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
  5 44  1  0  0  0  0
  6 45  1  0  0  0  0
M  END
$$$$

MOL SMILES InChIKey

Compound Description

A natural product found in Alstonia spatulata.

Identification

Molecular Formula

C19H22N2O2

Mass

310.39020

Monoisotopic Mass

310.16813

Charge

InChI

InChI=1S/C19H22N2O2/c1-2-18-9-5-11-20-17(23)12-14-13-6-3-4-7-15(13)21(19(14,18)20)16(22)8-10-18/h3-4,6-7,14H,2,5,8-12H2,1H3/t14-,18+,19?/m0/s1

InChIKey

RNBQHSCFWXNVOE-BQGOGBDGSA-N

SMILES

[H][C@]12CC(=O)N3CCC[C@]4(CC)CCC(=O)N(c5ccccc15)C234

Species

alstonia spatulata

IPNI:76595-1 21043460

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Europe PubMed Central results

Strychnan and secoangustilobine A type alkaloids from Alstonia spatulata. Revision of the C-20 configuration of scholaricine.

Author: Tan SJ, Low YY, Choo YM, Abdullah Z, Etoh T, Hayashi M, Komiyama K, Kam TS.

Abstract: A total of 25 alkaloids were isolated from the leaf and stem-bark extracts of Alstonia spatulata, of which five are new alkaloids of the strychnan type (alstolucines A-E, 1-5) and the other, a new alkaloid of the secoangustilobine A type (alstolobine A, 6). The structures of these alkaloids were established using NMR and MS analysis and, in the case of alstolucine B (2), also confirmed by X-ray diffraction analysis. A reinvestigation of the stereochemical assignment of scholaricine (13) by NMR and X-ray analyses indicated that the configuration at C-20 required revision. Alkaloids 1, 2, 6, 7, 9, 10, and 13 reversed multidrug resistance in vincristine-resistant KB cells.

DOI: 10.1021/np100552b

Connect to another EMBL location

MTBLC70514: leuconoxine

A natural product found in Alstonia spatulata.

Identification

Species

Europe PubMed Central results

Strychnan and secoangustilobine A type alkaloids from Alstonia spatulata. Revision of the C-20 configuration of scholaricine.

Author: Tan SJ, Low YY, Choo YM, Abdullah Z, Etoh T, Hayashi M, Komiyama K, Kam TS.