NP-MRD: Showing NP-Card for raucaffrinoline (NP0258017)

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Record Information

Version

2.0

Created at

2022-09-07 23:18:26 UTC

Updated at

2022-09-07 23:18:26 UTC

NP-MRD ID

NP0258017

Secondary Accession Numbers

None

Natural Product Identification

Common Name

raucaffrinoline

Description

Raucaffrinoline belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether. raucaffrinoline is found in Alstonia yunnanensis, Rauvolfia bahiensis, Rauvolfia sellowii, Rauvolfia semperflorens, Rauvolfia serpentina and Rauvolfia volkensii. raucaffrinoline was first documented in 2002 (PMID: 12031452). Based on a literature review a small amount of articles have been published on raucaffrinoline (PMID: 23707746) (PMID: 23159924) (PMID: 22334702) (PMID: 17142919).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082201182D          

 26 31  0  0  1  0            999 V2000
    3.5860   -3.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5130   -2.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1881   -1.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7648   -1.8436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -1.0218    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0582   -0.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144    0.4068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4239    1.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1193    0.7650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9638    0.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312    1.0504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2444    0.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0605    0.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5730   -0.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2692   -0.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4531   -0.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9407   -0.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0958   -0.3054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2197   -0.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2648    0.3063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6992   -0.4121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9190   -0.8151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6921   -1.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5046   -0.1189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3097    0.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -0.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 10  1  1  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  1  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 50 55  0  0  0  0  0  0  0  0999 V2000
    1.6005   -1.6465    4.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -0.6435    3.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4261    0.5956    3.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8197   -0.9733    1.9884 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5041   -0.0580    0.9659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9320   -0.2899    0.5847 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6949    1.0221    0.4453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9201    1.9851   -0.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208    1.1833   -1.5799 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0615    0.7726   -1.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2305    1.1756   -1.6003 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2628    0.4095   -0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6249    0.5420   -1.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4027   -0.3455   -0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8363   -1.2961    0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4546   -1.4122    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6698   -0.5429   -0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2405   -0.3473   -0.3152 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4734   -1.5231   -0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9526   -0.9617   -0.7579 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1743    0.0268   -1.8187 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5696    0.4089   -1.7395 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4518   -0.6570   -2.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9709    0.6724   -0.3064 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0159    1.7513   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1316    1.3383   -0.8899 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6052   -2.0576    4.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4106   -1.1554    5.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8468   -2.4761    4.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6593    0.9957    1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4873   -0.9021    1.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8873    1.4392    1.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6430    2.7118   -0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1262    2.5146    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3111    1.8260   -2.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0919    1.2866   -1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4862   -0.2288   -0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4987   -1.9610    0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0338   -2.1715    1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5292   -2.3349   -0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7333   -1.7997   -1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7069   -1.7530   -0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    1.3794   -2.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0333   -1.1967   -1.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2155   -0.2191   -3.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8587   -1.4271   -2.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3506   -0.2770    0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2223    1.8862    0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671    2.6906   -0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4468    2.0435   -1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 24  7  1  0
  7  8  1  0
  8  9  1  0
  9 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5  6  1  0
 18 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 21 22  1  0
  6 20  1  0
 17 12  1  0
  6  7  1  0
 10  9  1  0
 18 17  1  1
 23 44  1  0
 23 45  1  0
 23 46  1  0
 22 43  1  6
 24 47  1  1
 25 48  1  0
 25 49  1  0
 26 50  1  0
  7 32  1  1
  8 33  1  0
  8 34  1  0
  9 35  1  6
 20 42  1  1
 19 40  1  0
 19 41  1  0
  5 30  1  1
  1 27  1  0
  1 28  1  0
  1 29  1  0
  6 31  1  1
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
M  END


  Mrv1652309082201182D          

 26 31  0  0  1  0            999 V2000
    3.5860   -3.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5130   -2.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1881   -1.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7648   -1.8436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -1.0218    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0582   -0.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144    0.4068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4239    1.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1193    0.7650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9638    0.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312    1.0504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2444    0.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0605    0.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5730   -0.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2692   -0.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4531   -0.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9407   -0.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0958   -0.3054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2197   -0.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2648    0.3063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6992   -0.4121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9190   -0.8151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6921   -1.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5046   -0.1189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3097    0.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8315   -0.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 10  1  1  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  1  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0258017

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H](CO)[C@@H]2C[C@@H]3N1[C@H]1C[C@]4([C@H](OC(C)=O)C21)C3=NC1=CC=CC=C41

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O3/c1-10-13(9-24)12-7-16-19-21(14-5-3-4-6-15(14)22-19)8-17(23(10)16)18(12)20(21)26-11(2)25/h3-6,10,12-13,16-18,20,24H,7-9H2,1-2H3/t10-,12-,13-,16-,17-,18?,20+,21+/m0/s1

> <INCHI_KEY>
XIMPCXFLDSKALH-FXRWJBKJSA-N

> <FORMULA>
C21H24N2O3

> <MOLECULAR_WEIGHT>
352.434

> <EXACT_MASS>
352.178692641

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.626890709070686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,10S,12S,13R,14S,16S,18R)-13-(hydroxymethyl)-14-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-18-yl acetate

> <JCHEM_LOGP>
1.6766495586666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.413437158472512

> <JCHEM_PKA_STRONGEST_BASIC>
6.526236922018582

> <JCHEM_POLAR_SURFACE_AREA>
62.129999999999995

> <JCHEM_REFRACTIVITY>
98.1086

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10S,12S,13R,14S,16S,18R)-13-(hydroxymethyl)-14-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-18-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       6.694  -5.624   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.558  -4.090   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.818  -3.205   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.161  -3.441   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.025  -1.907   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.842  -0.477   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.080   0.759   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.658   2.157   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.956   1.428   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.532   1.081   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.778   1.961   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       7.923   0.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.446   1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.403  -0.052   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.836  -1.483   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.312  -1.708   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.356  -0.501   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.779  -0.570   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.143  -1.428   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.228   0.572   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.172  -0.769   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       1.715  -1.522   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.292  -3.002   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.942  -0.222   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.578   0.025   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.552  -1.168   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   10    5   19                                             
CONECT   19   18   20                                                       
CONECT   20   19    6   21                                                  
CONECT   21   20    9   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    7   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

View in JSmol

Synonyms

Value	Source
(17R,20alpha,21beta)-1,2-Didehydro-1-demethyl-19-hydroxy-21-methyl-18-norajmalan-17-yl acetate	ChEBI
(17R,20a,21b)-1,2-Didehydro-1-demethyl-19-hydroxy-21-methyl-18-norajmalan-17-yl acetate	Generator
(17R,20a,21b)-1,2-Didehydro-1-demethyl-19-hydroxy-21-methyl-18-norajmalan-17-yl acetic acid	Generator
(17R,20alpha,21beta)-1,2-Didehydro-1-demethyl-19-hydroxy-21-methyl-18-norajmalan-17-yl acetic acid	Generator
(17R,20Α,21β)-1,2-didehydro-1-demethyl-19-hydroxy-21-methyl-18-norajmalan-17-yl acetate	Generator
(17R,20Α,21β)-1,2-didehydro-1-demethyl-19-hydroxy-21-methyl-18-norajmalan-17-yl acetic acid	Generator

Chemical Formula

C₂₁H₂₄N₂O₃

Average Mass

352.4340 Da

Monoisotopic Mass

352.17869 Da

IUPAC Name

(1R,10S,12S,13R,14S,16S,18R)-13-(hydroxymethyl)-14-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-18-yl acetate

Traditional Name

(1R,10S,12S,13R,14S,16S,18R)-13-(hydroxymethyl)-14-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-18-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H](CO)[C@@H]2C[C@@H]3N1[C@H]1C[C@]4([C@H](OC(C)=O)C21)C3=NC1=CC=CC=C41

InChI Identifier

InChI=1S/C21H24N2O3/c1-10-13(9-24)12-7-16-19-21(14-5-3-4-6-15(14)22-19)8-17(23(10)16)18(12)20(21)26-11(2)25/h3-6,10,12-13,16-18,20,24H,7-9H2,1-2H3/t10-,12-,13-,16-,17-,18?,20+,21+/m0/s1

InChI Key

XIMPCXFLDSKALH-FXRWJBKJSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Alstonia yunnanensis	LOTUS Database	35616633
Rauvolfia bahiensis	LOTUS Database	35616633
Rauvolfia sellowii	LOTUS Database	35616633
Rauvolfia semperflorens	LOTUS Database	35616633
Rauvolfia serpentina	LOTUS Database	35616633
Rauvolfia volkensii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ajmaline-sarpagine alkaloids

Sub Class

Not Available

Direct Parent

Ajmaline-sarpagine alkaloids

Alternative Parents

Substituents

Sarpagine-skeleton
Quinolizidine
3-alkylindole
Indole or derivatives
Quinuclidine
Azepane
Aralkylamine
Piperidine
Benzenoid
1,3-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Ketimine
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Alcohol
Organic oxygen compound
Imine
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Amine
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indole alkaloid (CHEBI:63167 )

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	1.68	ChemAxon
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	6.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	98.11 m³·mol⁻¹	ChemAxon
Polarizability	38.63 Å³	ChemAxon
Number of Rings	6	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

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024282

Chemspider ID

26332998

KEGG Compound ID

C19931

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Raucaffrinoline

METLIN ID

Not Available

PubChem Compound

56927714

PDB ID

Not Available

ChEBI ID

63167

Good Scents ID

Not Available

References

General References

Geng CA, Liu XK: Five new indole alkaloids from the leaves of Rauvolfia yunnanensis. Fitoterapia. 2013 Sep;89:42-7. doi: 10.1016/j.fitote.2013.05.017. Epub 2013 May 23. [PubMed:23707746 ]
Cao P, Liang Y, Gao X, Li XM, Song ZQ, Liang G: Monoterpenoid indole alkaloids from Alstonia yunnanensis and their cytotoxic and anti-inflammatory activities. Molecules. 2012 Nov 16;17(11):13631-41. doi: 10.3390/molecules171113631. [PubMed:23159924 ]
Sun L, Chen Y, Rajendran C, Mueller U, Panjikar S, Wang M, Mindnich R, Rosenthal C, Penning TM, Stockigt J: Crystal structure of perakine reductase, founding member of a novel aldo-keto reductase (AKR) subfamily that undergoes unique conformational changes during NADPH binding. J Biol Chem. 2012 Mar 30;287(14):11213-21. doi: 10.1074/jbc.M111.335521. Epub 2012 Feb 13. [PubMed:22334702 ]
Rosenthal C, Mueller U, Panjikar S, Sun L, Ruppert M, Zhao Y, Stockigt J: Expression, purification, crystallization and preliminary X-ray analysis of perakine reductase, a new member of the aldo-keto reductase enzyme superfamily from higher plants. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2006 Dec 1;62(Pt 12):1286-9. doi: 10.1107/S174430910605041X. Epub 2006 Nov 30. [PubMed:17142919 ]
Kato L, Marques Braga R, Koch I, Sumiko Kinoshita L: Indole alkaloids from Rauvolfia bahiensis A.DC. (Apocynaceae). Phytochemistry. 2002 Jun;60(3):315-20. doi: 10.1016/s0031-9422(02)00122-x. [PubMed:12031452 ]
LOTUS database [Link]

Showing NP-Card for raucaffrinoline (NP0258017)

MOL for NP0258017 (raucaffrinoline)

3D MOL for NP0258017 (raucaffrinoline)

3D SDF for NP0258017 (raucaffrinoline)

3D-SDF for NP0258017 (raucaffrinoline)

PDB for NP0258017 (raucaffrinoline)

3D PDB for NP0258017 (raucaffrinoline)

SMILES for NP0258017 (raucaffrinoline)

INCHI for NP0258017 (raucaffrinoline)

Structure for NP0258017 (raucaffrinoline)

3D Structure for NP0258017 (raucaffrinoline)