NP-MRD: Showing NP-Card for Vincamine (NP0050918)

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Record Information

Version

2.0

Created at

2022-04-27 22:23:07 UTC

Updated at

2022-04-27 22:23:08 UTC

NP-MRD ID

NP0050918

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vincamine

Description

Vincamine, also known as vincamidol or cetal retard, belongs to the class of organic compounds known as eburnan-type alkaloids. These are alkaloids with a structure based on the eburnan skeleton, that arises from rearrangement of the aspidospermidine ring system, involving migration of C-21 from C-7 to C-2, fission of the 2,16-bond, and attachment of C-16 to N-1. In the United States, it is permitted to be sold as a dietary supplement when labeled for use in adults for six months or less. Vincamine is a monoterpenoid indole alkaloid found in the leaves of Vinca minor (lesser periwinkle), comprising about 25-65% of its indole alkaloids by weight. Vincamine is sold in Europe as a prescription medicine for the treatment of primary degenerative and vascular dementia. Vincamine is a very strong basic compound (based on its pKa). Vinpocetine is a synthetic derivative of vincamine. It can also be synthesized from related alkaloids. Vincamine is found in Apis cerana, Catharanthus roseus , Vinca erecta Rgl.et Schmalh., Vinca herbacea Waldst.et Kit. , Vinca major , Vinca minor and Vinca sp.. Most common preparations are in the sustained release tablet forms.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004221604022D          

 27 31  0  0  1  0            999 V2000
    0.6869    0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069    2.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106    0.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913   -1.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521   -0.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053   -0.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0972   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -2.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579   -0.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763   -1.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1709   -2.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    0.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640   -1.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4472   -1.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762   -0.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526   -0.8721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0613    1.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816   -0.1353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1579    0.5073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7999   -1.5619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289   -0.2296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226    1.8200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480    0.7447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3035    1.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7052   -0.1824    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  1  0  0  0  0
 12  9  1  0  0  0  0
 14  7  2  0  0  0  0
 15  9  1  0  0  0  0
 15 14  1  0  0  0  0
 16  8  2  0  0  0  0
 16 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 17  1  0  0  0  0
 20  3  1  6  0  0  0
 20 10  1  0  0  0  0
 20 13  1  0  0  0  0
 20 18  1  0  0  0  0
 21 13  1  0  0  0  0
 21 19  1  6  0  0  0
 22 11  1  0  0  0  0
 22 12  1  0  0  0  0
 22 18  1  0  0  0  0
 23 16  1  0  0  0  0
 23 17  1  0  0  0  0
 23 21  1  0  0  0  0
 24 19  2  0  0  0  0
 21 25  1  1  0  0  0
 26  2  1  0  0  0  0
 26 19  1  0  0  0  0
 18 27  1  6  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -2.6830    2.1140    1.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1161    1.8740    0.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3925    0.5318    0.6151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4170   -0.5923    0.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5793   -0.4119   -0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0548   -0.3129   -1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625   -0.4507   -1.6143 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233   -1.3095   -2.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063   -1.7033   -2.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9774   -1.4119   -1.4399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4768   -0.4941   -0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3153   -0.3853    0.4562 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3759   -1.2204    0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5074   -1.5031    0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4151   -2.4420    0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2033   -3.0875   -0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0608   -2.7966   -1.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549   -1.8614   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958    0.5392    1.5290 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5866    0.0316    2.7202 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112    1.8372    1.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4481    2.3096    2.0883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3093    2.5979    0.1775 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8894    3.8618   -0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4672    0.5187    1.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7957    0.2199   -0.7415 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7055    1.1995    2.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236    2.9433    2.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7371    2.4720    1.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9391    1.9254   -0.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4018    2.6516    0.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8939   -1.5298    0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6743   -0.7130    1.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240   -1.3328    0.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2568    0.4201    0.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5306   -1.1666   -2.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4538    0.5940   -2.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4946   -0.8816   -3.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8373   -2.2593   -2.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7489   -1.1879   -3.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356   -2.7914   -2.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6693   -0.9961    1.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3107   -2.6743    1.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8845   -3.8179   -1.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8832   -3.3016   -2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284   -0.8030    2.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8276    3.7205   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1584    4.4008   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1007    4.4372    0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818    1.4009    2.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805   -0.3658    2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5549    1.2027   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
 26  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  6
  2  1  1  0
  3 25  1  0
 25 19  1  0
 19 20  1  1
 19 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 10  1  0
 10  9  1  0
  9  8  1  0
 10 11  2  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
  3 26  1  0
 11 12  1  0
 11 26  1  0
  8  7  1  0
 18 13  1  0
 26 52  1  6
  6 36  1  0
  6 37  1  0
  5 34  1  0
  5 35  1  0
  4 32  1  0
  4 33  1  0
  2 30  1  0
  2 31  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 25 50  1  0
 25 51  1  0
 20 46  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
  9 40  1  0
  9 41  1  0
  8 38  1  0
  8 39  1  0
 24 47  1  0
 24 48  1  0
 24 49  1  0
M  END


  Mrv1572004221604022D          

 27 31  0  0  1  0            999 V2000
    0.6869    0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069    2.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106    0.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913   -1.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521   -0.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053   -0.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0972   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -2.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579   -0.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763   -1.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1709   -2.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    0.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640   -1.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4472   -1.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762   -0.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526   -0.8721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0613    1.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816   -0.1353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1579    0.5073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7999   -1.5619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289   -0.2296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226    1.8200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9480    0.7447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3035    1.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7052   -0.1824    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  1  0  0  0  0
 12  9  1  0  0  0  0
 14  7  2  0  0  0  0
 15  9  1  0  0  0  0
 15 14  1  0  0  0  0
 16  8  2  0  0  0  0
 16 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 17  1  0  0  0  0
 20  3  1  6  0  0  0
 20 10  1  0  0  0  0
 20 13  1  0  0  0  0
 20 18  1  0  0  0  0
 21 13  1  0  0  0  0
 21 19  1  6  0  0  0
 22 11  1  0  0  0  0
 22 12  1  0  0  0  0
 22 18  1  0  0  0  0
 23 16  1  0  0  0  0
 23 17  1  0  0  0  0
 23 21  1  0  0  0  0
 24 19  2  0  0  0  0
 21 25  1  1  0  0  0
 26  2  1  0  0  0  0
 26 19  1  0  0  0  0
 18 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050918

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12N3CCC[C@@]1(CC)C[C@@](O)(N1C4=CC=CC=C4C(CC3)=C21)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+/m1/s1

> <INCHI_KEY>
RXPRRQLKFXBCSJ-GIVPXCGWSA-N

> <FORMULA>
C21H26N2O3

> <MOLECULAR_WEIGHT>
354.45

> <EXACT_MASS>
354.194342705

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.38673737303381

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
3.3907502936666667

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.520702993749815

> <JCHEM_PKA_STRONGEST_BASIC>
6.699323210636179

> <JCHEM_POLAR_SURFACE_AREA>
54.7

> <JCHEM_REFRACTIVITY>
99.5741

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
minorin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       1.282   1.211   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.119   4.614   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.820   1.123   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.810  -2.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.737  -0.707   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.130  -1.452   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.515  -3.078   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.368  -0.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.590  -4.379   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.975  -0.164   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.822  -2.827   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.052  -4.291   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.357   1.035   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.146  -2.373   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.435  -3.092   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.073  -0.834   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.742  -1.716   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.205  -1.628   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.714   2.476   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.512  -0.253   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.895   0.947   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       3.360  -2.916   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       6.587  -0.429   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       6.949   3.397   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.370   1.390   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.300   3.085   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       5.050  -0.341   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2   26                                                            
CONECT    3    1   20                                                       
CONECT    4    5    7                                                       
CONECT    5    4    8                                                       
CONECT    6   10   11                                                       
CONECT    7    4   14                                                       
CONECT    8    5   16                                                       
CONECT    9   12   15                                                       
CONECT   10    6   20                                                       
CONECT   11    6   22                                                       
CONECT   12    9   22                                                       
CONECT   13   20   21                                                       
CONECT   14    7   15   16                                                  
CONECT   15    9   14   17                                                  
CONECT   16    8   14   23                                                  
CONECT   17   15   18   23                                                  
CONECT   18   17   20   22   27                                             
CONECT   19   21   24   26                                                  
CONECT   20    3   10   13   18                                             
CONECT   21   13   19   23   25                                             
CONECT   22   11   12   18                                                  
CONECT   23   16   17   21                                                  
CONECT   24   19                                                            
CONECT   25   21                                                            
CONECT   26    2   19                                                       
CONECT   27   18                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
(+)-Vincamine	ChEBI
Methyl vincaminate	ChEBI
Pervincamine	ChEBI
Vincamidol	ChEBI
Cetal retard	Kegg
Methyl vincaminic acid	Generator
Devincan	MeSH
Vincimax	MeSH
Vincapront	MeSH
Cerebroxine	MeSH

Chemical Formula

C₂₁H₂₆N₂O₃

Average Mass

354.4500 Da

Monoisotopic Mass

354.19434 Da

IUPAC Name

methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

Traditional Name

minorin

CAS Registry Number

Not Available

SMILES

[H][C@]12N3CCC[C@@]1(CC)C[C@@](O)(N1C4=CC=CC=C4C(CC3)=C21)C(=O)OC

InChI Identifier

InChI=1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+/m1/s1

InChI Key

RXPRRQLKFXBCSJ-GIVPXCGWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Catharanthus roseus	Plant	KNApSAcK
Vinca erecta Rgl.et Schmalh.	Plant	KNApSAcK
Vinca herbacea Waldst.et Kit.	Plant	KNApSAcK
Vinca major	Plant	KNApSAcK
Vinca minor	Plant	KNApSAcK
Vinca sp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eburnan-type alkaloids. These are alkaloids with a structure based on the eburnan skeleton, that arises from rearrangement of the aspidospermidine ring system, involving migration of C-21 from C-7 to C-2, fission of the 2,16-bond, and attachment of C-16 to N-1.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Eburnan-type alkaloids

Sub Class

Not Available

Direct Parent

Eburnan-type alkaloids

Alternative Parents

Substituents

Eburna alkaloid
Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Diazanaphthalene
Alpha-amino acid or derivatives
Naphthyridine
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Piperidine
Benzenoid
Heteroaromatic compound
Methyl ester
Pyrrole
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Alkanolamine
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:9985 )
methyl ester (CHEBI:9985 )
hemiaminal (CHEBI:9985 )
alkaloid ester (CHEBI:9985 )
vinca alkaloid (CHEBI:9985 )
Indole alkaloids (C09251 )

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	2.62	ALOGPS
logP	3.39	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.52	ChemAxon
pKa (Strongest Basic)	6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.7 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.57 m³·mol⁻¹	ChemAxon
Polarizability	39.39 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB13374

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001782

Chemspider ID

Not Available

KEGG Compound ID

C09251

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vincamine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

9985

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Vincamine (NP0050918)

MOL for NP0050918 (Vincamine)

3D MOL for NP0050918 (Vincamine)

3D SDF for NP0050918 (Vincamine)

3D-SDF for NP0050918 (Vincamine)

PDB for NP0050918 (Vincamine)

3D PDB for NP0050918 (Vincamine)

SMILES for NP0050918 (Vincamine)

INCHI for NP0050918 (Vincamine)

Structure for NP0050918 (Vincamine)

3D Structure for NP0050918 (Vincamine)