NP-MRD: Showing NP-Card for genipamide (NP0032822)

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Record Information

Version

2.0

Created at

2021-06-19 23:32:08 UTC

Updated at

2021-06-30 00:02:14 UTC

NP-MRD ID

NP0032822

Secondary Accession Numbers

None

Natural Product Identification

Common Name

genipamide

Provided By

JEOL Database JEOL Logo

Description

(4AS)-1-Oxo-4-(methoxycarbonyl)-7-(hydroxymethyl)-1,2,4aalpha,7aalpha-tetrahydro-5H-cyclopenta[c]pyridine-2-butanoic acid methyl ester belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group. genipamide is found in Genipa americana. genipamide was first documented in 2007 (Ono, M., et al.). Based on a literature review very few articles have been published on (4aS)-1-Oxo-4-(methoxycarbonyl)-7-(hydroxymethyl)-1,2,4aalpha,7aalpha-tetrahydro-5H-cyclopenta[c]pyridine-2-butanoic acid methyl ester.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101323D          

 44 45  0  0  0  0            999 V2000
   -1.0264    4.2298   -2.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4626    3.0199   -1.6936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416    3.1423   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7435    4.1883    0.2672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0972    1.7901    0.2030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8588    1.7068    1.7113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3905    1.8644    2.1319 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4820    0.8149    1.5841 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567   -0.4309    2.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115   -1.4894    1.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0571   -2.8271    2.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6277   -3.8079    1.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3083   -2.8054    3.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -4.0668    4.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322   -1.3900    0.4398 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2498   -2.0498   -0.7735 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7214   -1.2168   -1.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2664   -0.0637   -1.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8650    0.9875   -2.3791 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9276    2.0212   -2.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594    0.0488    0.0023 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2783    1.1217    0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514    2.2306   -0.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7684    4.0056   -3.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346    4.6196   -1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8307    4.9719   -2.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1577    1.6145   -0.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5206    1.0132   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389    0.7417    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482    2.4807    2.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3202    1.8262    3.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0161    2.8518    1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1612   -0.5095    3.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2171   -4.4014    4.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501   -4.8110    3.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970   -3.9382    5.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8941   -1.8979    0.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1557   -2.0266   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5733   -3.0897   -0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6107   -1.5112   -2.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627    1.4154   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591    0.5699   -3.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.3346   -1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530    0.3272    0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 15 10  1  0  0  0  0
  5  3  1  0  0  0  0
 21 22  1  0  0  0  0
  3  2  1  0  0  0  0
 22  8  1  0  0  0  0
  2  1  1  0  0  0  0
  8  9  1  0  0  0  0
 15 37  1  1  0  0  0
 15 16  1  0  0  0  0
 21 44  1  1  0  0  0
 16 17  1  0  0  0  0
 22 23  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 20  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  8  7  1  0  0  0  0
 11 13  1  0  0  0  0
 21 15  1  0  0  0  0
 11 12  2  0  0  0  0
  7  6  1  0  0  0  0
 13 14  1  0  0  0  0
  3  4  2  0  0  0  0
  9 33  1  0  0  0  0
 16 38  1  0  0  0  0
 16 39  1  0  0  0  0
 17 40  1  0  0  0  0
  7 31  1  0  0  0  0
  7 32  1  0  0  0  0
  6 29  1  0  0  0  0
  6 30  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 20 43  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
M  END

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -1.0264    4.2298   -2.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4626    3.0199   -1.6936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416    3.1423   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7435    4.1883    0.2672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0972    1.7901    0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588    1.7068    1.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3905    1.8644    2.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820    0.8149    1.5841 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567   -0.4309    2.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115   -1.4894    1.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0571   -2.8271    2.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6277   -3.8079    1.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3083   -2.8054    3.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -4.0668    4.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322   -1.3900    0.4398 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2498   -2.0498   -0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7214   -1.2168   -1.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2664   -0.0637   -1.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8650    0.9875   -2.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9276    2.0212   -2.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594    0.0488    0.0023 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2783    1.1217    0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514    2.2306   -0.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7684    4.0056   -3.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346    4.6196   -1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8307    4.9719   -2.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1577    1.6145   -0.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5206    1.0132   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389    0.7417    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482    2.4807    2.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3202    1.8262    3.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0161    2.8518    1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1612   -0.5095    3.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2171   -4.4014    4.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501   -4.8110    3.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970   -3.9382    5.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8941   -1.8979    0.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1557   -2.0266   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5733   -3.0897   -0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6107   -1.5112   -2.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627    1.4154   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591    0.5699   -3.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.3346   -1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530    0.3272    0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
 15 10  1  0
  5  3  1  0
 21 22  1  0
  3  2  1  0
 22  8  1  0
  2  1  1  0
  8  9  1  0
 15 37  1  1
 15 16  1  0
 21 44  1  1
 16 17  1  0
 22 23  2  0
 17 18  2  0
 18 19  1  0
 18 21  1  0
 19 20  1  0
  9 10  2  0
 10 11  1  0
  8  7  1  0
 11 13  1  0
 21 15  1  0
 11 12  2  0
  7  6  1  0
 13 14  1  0
  3  4  2  0
  9 33  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
  7 31  1  0
  7 32  1  0
  6 29  1  0
  6 30  1  0
  5 27  1  0
  5 28  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
M  END


  Mrv1652306202101323D          

 44 45  0  0  0  0            999 V2000
   -1.0264    4.2298   -2.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4626    3.0199   -1.6936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416    3.1423   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7435    4.1883    0.2672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0972    1.7901    0.2030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8588    1.7068    1.7113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3905    1.8644    2.1319 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4820    0.8149    1.5841 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567   -0.4309    2.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115   -1.4894    1.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0571   -2.8271    2.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6277   -3.8079    1.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3083   -2.8054    3.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -4.0668    4.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322   -1.3900    0.4398 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2498   -2.0498   -0.7735 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7214   -1.2168   -1.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2664   -0.0637   -1.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8650    0.9875   -2.3791 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9276    2.0212   -2.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594    0.0488    0.0023 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2783    1.1217    0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514    2.2306   -0.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7684    4.0056   -3.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346    4.6196   -1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8307    4.9719   -2.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1577    1.6145   -0.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5206    1.0132   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389    0.7417    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482    2.4807    2.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3202    1.8262    3.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0161    2.8518    1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1612   -0.5095    3.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2171   -4.4014    4.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501   -4.8110    3.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970   -3.9382    5.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8941   -1.8979    0.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1557   -2.0266   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5733   -3.0897   -0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6107   -1.5112   -2.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627    1.4154   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591    0.5699   -3.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.3346   -1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530    0.3272    0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 15 10  1  0  0  0  0
  5  3  1  0  0  0  0
 21 22  1  0  0  0  0
  3  2  1  0  0  0  0
 22  8  1  0  0  0  0
  2  1  1  0  0  0  0
  8  9  1  0  0  0  0
 15 37  1  1  0  0  0
 15 16  1  0  0  0  0
 21 44  1  1  0  0  0
 16 17  1  0  0  0  0
 22 23  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 20  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  8  7  1  0  0  0  0
 11 13  1  0  0  0  0
 21 15  1  0  0  0  0
 11 12  2  0  0  0  0
  7  6  1  0  0  0  0
 13 14  1  0  0  0  0
  3  4  2  0  0  0  0
  9 33  1  0  0  0  0
 16 38  1  0  0  0  0
 16 39  1  0  0  0  0
 17 40  1  0  0  0  0
  7 31  1  0  0  0  0
  7 32  1  0  0  0  0
  6 29  1  0  0  0  0
  6 30  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 20 43  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032822

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C([H])C([H])([H])[C@]2([H])C(=C([H])N(C(=O)[C@]12[H])C([H])([H])C([H])([H])C([H])([H])C(=O)OC([H])([H])[H])C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO6/c1-22-13(19)4-3-7-17-8-12(16(21)23-2)11-6-5-10(9-18)14(11)15(17)20/h5,8,11,14,18H,3-4,6-7,9H2,1-2H3/t11-,14-/m1/s1

> <INCHI_KEY>
KVMRRASZAWOPTJ-BXUZGUMPSA-N

> <FORMULA>
C16H21NO6

> <MOLECULAR_WEIGHT>
323.345

> <EXACT_MASS>
323.1368874

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.67883383178507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (4aS,7aS)-7-(hydroxymethyl)-2-(4-methoxy-4-oxobutyl)-1-oxo-1H,2H,4aH,5H,7aH-cyclopenta[c]pyridine-4-carboxylate

> <ALOGPS_LOGP>
0.69

> <JCHEM_LOGP>
-0.5240363616666668

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.13607918555017

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7392789642403548

> <JCHEM_POLAR_SURFACE_AREA>
93.14000000000001

> <JCHEM_REFRACTIVITY>
82.02029999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4aS,7aS)-7-(hydroxymethyl)-2-(4-methoxy-4-oxobutyl)-1-oxo-4aH,5H,7aH-cyclopenta[c]pyridine-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -1.0264    4.2298   -2.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4626    3.0199   -1.6936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416    3.1423   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7435    4.1883    0.2672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0972    1.7901    0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588    1.7068    1.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3905    1.8644    2.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820    0.8149    1.5841 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567   -0.4309    2.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115   -1.4894    1.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0571   -2.8271    2.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6277   -3.8079    1.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3083   -2.8054    3.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -4.0668    4.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322   -1.3900    0.4398 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2498   -2.0498   -0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7214   -1.2168   -1.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2664   -0.0637   -1.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8650    0.9875   -2.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9276    2.0212   -2.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594    0.0488    0.0023 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2783    1.1217    0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514    2.2306   -0.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7684    4.0056   -3.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346    4.6196   -1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8307    4.9719   -2.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1577    1.6145   -0.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5206    1.0132   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389    0.7417    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482    2.4807    2.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3202    1.8262    3.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0161    2.8518    1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1612   -0.5095    3.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2171   -4.4014    4.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501   -4.8110    3.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970   -3.9382    5.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8941   -1.8979    0.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1557   -2.0266   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5733   -3.0897   -0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6107   -1.5112   -2.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627    1.4154   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591    0.5699   -3.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.3346   -1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530    0.3272    0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
 15 10  1  0
  5  3  1  0
 21 22  1  0
  3  2  1  0
 22  8  1  0
  2  1  1  0
  8  9  1  0
 15 37  1  1
 15 16  1  0
 21 44  1  1
 16 17  1  0
 22 23  2  0
 17 18  2  0
 18 19  1  0
 18 21  1  0
 19 20  1  0
  9 10  2  0
 10 11  1  0
  8  7  1  0
 11 13  1  0
 21 15  1  0
 11 12  2  0
  7  6  1  0
 13 14  1  0
  3  4  2  0
  9 33  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
  7 31  1  0
  7 32  1  0
  6 29  1  0
  6 30  1  0
  5 27  1  0
  5 28  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.026   4.230  -2.313  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.463   3.020  -1.694  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.742   3.142  -0.368  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.744   4.188   0.267  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.097   1.790   0.203  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.859   1.707   1.711  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.391   1.864   2.132  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.482   0.815   1.584  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.457  -0.431   2.182  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.111  -1.489   1.689  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.057  -2.827   2.339  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.628  -3.808   1.886  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.308  -2.805   3.470  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.224  -4.067   4.135  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.932  -1.390   0.440  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.250  -2.050  -0.774  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.721  -1.217  -1.916  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.266  -0.064  -1.505  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.865   0.988  -2.379  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.928   2.021  -2.623  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.259   0.049   0.002  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.278   1.122   0.483  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.251   2.231  -0.061  0.00  0.00           O+0
HETATM   24  H   UNK     0      -0.768   4.006  -3.351  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.135   4.620  -1.811  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.831   4.972  -2.306  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.158   1.615  -0.010  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.521   1.013  -0.310  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.239   0.742   2.068  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.448   2.481   2.218  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.320   1.826   3.227  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.016   2.852   1.842  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.161  -0.509   3.074  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.217  -4.401   4.450  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.250  -4.811   3.487  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.397  -3.938   5.026  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.894  -1.898   0.611  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.156  -2.027  -0.717  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.573  -3.090  -0.886  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.611  -1.511  -2.952  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.763   1.415  -1.922  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.159   0.570  -3.348  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.611   2.335  -1.749  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.253   0.327   0.376  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6    3   27   28                                             
CONECT    6    5    7   29   30                                             
CONECT    7    8    6   31   32                                             
CONECT    8   22    9    7                                                  
CONECT    9    8   10   33                                                  
CONECT   10   15    9   11                                                  
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   34   35   36                                             
CONECT   15   10   37   16   21                                             
CONECT   16   15   17   38   39                                             
CONECT   17   16   18   40                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   20   41   42                                             
CONECT   20   19   43                                                       
CONECT   21   22   44   18   15                                             
CONECT   22   21    8   23                                                  
CONECT   23   22                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    5                                                            
CONECT   28    5                                                            
CONECT   29    6                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
CONECT   32    7                                                            
CONECT   33    9                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   16                                                            
CONECT   39   16                                                            
CONECT   40   17                                                            
CONECT   41   19                                                            
CONECT   42   19                                                            
CONECT   43   20                                                            
CONECT   44   21                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

RDKit          3D

44 45  0  0  0  0  0  0  0  0999 V2000
   -1.0264    4.2298   -2.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4626    3.0199   -1.6936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416    3.1423   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7435    4.1883    0.2672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0972    1.7901    0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588    1.7068    1.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3905    1.8644    2.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820    0.8149    1.5841 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567   -0.4309    2.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115   -1.4894    1.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0571   -2.8271    2.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6277   -3.8079    1.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3083   -2.8054    3.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -4.0668    4.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322   -1.3900    0.4398 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2498   -2.0498   -0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7214   -1.2168   -1.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2664   -0.0637   -1.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8650    0.9875   -2.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9276    2.0212   -2.6226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594    0.0488    0.0023 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2783    1.1217    0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514    2.2306   -0.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7684    4.0056   -3.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346    4.6196   -1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8307    4.9719   -2.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1577    1.6145   -0.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5206    1.0132   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389    0.7417    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482    2.4807    2.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3202    1.8262    3.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0161    2.8518    1.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1612   -0.5095    3.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2171   -4.4014    4.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501   -4.8110    3.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3970   -3.9382    5.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8941   -1.8979    0.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1557   -2.0266   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5733   -3.0897   -0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6107   -1.5112   -2.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627    1.4154   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1591    0.5699   -3.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.3346   -1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530    0.3272    0.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
 15 10  1  0
  5  3  1  0
 21 22  1  0
  3  2  1  0
 22  8  1  0
  2  1  1  0
  8  9  1  0
 15 37  1  1
 15 16  1  0
 21 44  1  1
 16 17  1  0
 22 23  2  0
 17 18  2  0
 18 19  1  0
 18 21  1  0
 19 20  1  0
  9 10  2  0
 10 11  1  0
  8  7  1  0
 11 13  1  0
 21 15  1  0
 11 12  2  0
  7  6  1  0
 13 14  1  0
  3  4  2  0
  9 33  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
  7 31  1  0
  7 32  1  0
  6 29  1  0
  6 30  1  0
  5 27  1  0
  5 28  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
M  END

View in JSmol

Synonyms

Value	Source
(4AS)-1-oxo-4-(methoxycarbonyl)-7-(hydroxymethyl)-1,2,4aalpha,7aalpha-tetrahydro-5H-cyclopenta[c]pyridine-2-butanoate methyl ester	Generator

Chemical Formula

C₁₆H₂₁NO₆

Average Mass

323.3450 Da

Monoisotopic Mass

323.13689 Da

IUPAC Name

methyl (4aS,7aS)-7-(hydroxymethyl)-2-(4-methoxy-4-oxobutyl)-1-oxo-1H,2H,4aH,5H,7aH-cyclopenta[c]pyridine-4-carboxylate

Traditional Name

methyl (4aS,7aS)-7-(hydroxymethyl)-2-(4-methoxy-4-oxobutyl)-1-oxo-4aH,5H,7aH-cyclopenta[c]pyridine-4-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C1=C([H])C([H])([H])[C@]2([H])C(=C([H])N(C(=O)[C@]12[H])C([H])([H])C([H])([H])C([H])([H])C(=O)OC([H])([H])[H])C(=O)OC([H])([H])[H]

InChI Identifier

InChI=1S/C16H21NO6/c1-22-13(19)4-3-7-17-8-12(16(21)23-2)11-6-5-10(9-18)14(11)15(17)20/h5,8,11,14,18H,3-4,6-7,9H2,1-2H3/t11-,14-/m1/s1

InChI Key

KVMRRASZAWOPTJ-BXUZGUMPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Genipa americana	JEOL database	Ono, M., et al, Chem. Pharm. Bull. 55, 632 (2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid methyl esters

Alternative Parents

Substituents

Tetrahydropyridine
Fatty acid methyl ester
Dicarboxylic acid or derivatives
Tertiary carboxylic acid amide
Methyl ester
Enoate ester
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Carboxamide group
Carboxylic acid ester
Lactam
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Organic oxide
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.69	ALOGPS
logP	-0.52	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	15.14	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	93.14 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	82.02 m³·mol⁻¹	ChemAxon
Polarizability	32.68 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17588533

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16655216

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ono, M., et al. (2007). Ono, M., et al, Chem. Pharm. Bull. 55, 632 (2007) . Chem. Pharm. Bull..

Showing NP-Card for genipamide (NP0032822)

MOL for NP0032822 (genipamide)

3D MOL for NP0032822 (genipamide)

3D SDF for NP0032822 (genipamide)

3D-SDF for NP0032822 (genipamide)

PDB for NP0032822 (genipamide)

3D PDB for NP0032822 (genipamide)

SMILES for NP0032822 (genipamide)

INCHI for NP0032822 (genipamide)

Structure for NP0032822 (genipamide)

3D Structure for NP0032822 (genipamide)