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enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:00 UTC

HMDB ID

HMDB0015495

Secondary Accession Numbers

HMDB15495

Metabolite Identification

Common Name

Ajmaline

Description

An alkaloid found in the root of Rauwolfia serpentina, among other plant sources. It is a class Ia antiarrhythmic agent that apparently acts by changing the shape and threshold of cardiac action potentials. Ajmaline produces potent sodium channel blocking effects and a very short half-life which makes it a very useful drug for acute intravenous treatments. The drug has been very popular in some countries for the treatment of atrial fibrillation in patients with the Wolff Parkinson White syndrome and in well tolerated monomorphic ventricular tachycardias. It has also been used for many years as a drug to challenge the conduction system of the heart in cases of bundle branch block and syncope. In these cases, abnormal prolongation of the HV interval has been taken as a proof for infrahisian conduction defects tributary for permanent pacemaker implantation.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0015495
     RDKit          3D
Ajmaline
 50 55  0  0  0  0  0  0  0  0999 V2000
   -4.3617   -1.1041    1.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7962   -1.3798    0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0873   -0.1662    0.0771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9300    0.2323    0.9988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4171    1.5187    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5392    1.0844   -0.8567 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8300    1.0494   -0.3435 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9149    1.2753   -1.2276 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9185    1.8389   -2.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0799    0.8134   -0.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    1.1333   -0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3903    0.5621    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0048   -0.3765    1.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6676   -0.6956    1.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6834   -0.1333    0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2461   -0.2739    0.2856 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8082   -1.4450   -0.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6971   -1.2840   -0.4577 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9160   -0.8682    0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429   -0.4397    1.5161 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9568   -1.4975    2.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0828   -0.1585   -1.3238 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5482   -0.1719   -1.3128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0703    0.8442   -2.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8293   -0.0824    1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1008   -1.8553    2.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5561   -1.1000    2.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -2.2942    0.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6703   -1.5362   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8037    0.7046    0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3366    0.4370    1.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8611    2.1394    1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432    2.0946   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6182    1.8185   -1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9630    1.7981    0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972    2.9544   -2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600    1.4176   -3.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8710    1.6752   -3.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7649    1.8799   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4323    0.8451    0.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7701   -0.8318    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4236   -1.4491    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1504   -1.3625   -1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0899   -2.3643   -0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2440   -2.1657   -0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2864   -1.7028    1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3587    0.4848    2.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3255   -1.2057    3.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8375   -1.1490   -1.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3237    0.4918   -3.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 23  3  1  0
 19  4  1  0
 22  6  1  0
 16  7  1  0
 15 10  1  0
 20 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  6
  4 31  1  1
  5 32  1  0
  5 33  1  0
  6 34  1  6
  7 35  1  1
  9 36  1  0
  9 37  1  0
  9 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  6
 19 46  1  0
 20 47  1  1
 21 48  1  0
 23 49  1  6
 24 50  1  0
M  END

 
  Mrv0541 02231215292D          

 24 29  0  0  1  0            999 V2000
   11.7974   -9.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7974  -10.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5118  -11.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2263  -10.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2263   -9.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5118   -9.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0110  -10.8561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4959  -10.1887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.0110   -9.5212    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.3163  -10.1024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.6519   -9.3488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1670   -8.6813    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3465   -8.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0700  -10.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4056   -9.6843    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.1949   -9.5493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.4412   -9.2138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0198   -9.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6353   -7.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1794   -8.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0522   -7.5825    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0110  -11.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4374   -7.0107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4429  -10.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  1  0  0  0
 12 19  1  1  0  0  0
 15 19  1  6  0  0  0
 17 20  1  6  0  0  0
  9 21  1  1  0  0  0
 21 19  1  0  0  0  0
  7 22  1  0  0  0  0
 21 23  1  6  0  0  0
 18 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015495

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[C@H]1[C@@H]2C[C@H]3[C@@H]4N(C)C5=CC=CC=C5[C@]44C[C@@H](C2[C@H]4O)N3[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3/t10-,11-,14-,15-,16?,17-,18+,19+,20+/m0/s1

> <INCHI_KEY>
CJDRUOGAGYHKKD-HEFSZTOGSA-N

> <FORMULA>
C20H26N2O2

> <MOLECULAR_WEIGHT>
326.4326

> <EXACT_MASS>
326.199428086

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.754044551980826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9R,10S,12R,13S,14R,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-14,18-diol

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
1.8508077869999995

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.329058596520166

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.28015557494178

> <JCHEM_PKA_STRONGEST_BASIC>
7.1953337407340285

> <JCHEM_POLAR_SURFACE_AREA>
46.94

> <JCHEM_REFRACTIVITY>
92.5658

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ajmaline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015495
     RDKit          3D
Ajmaline
 50 55  0  0  0  0  0  0  0  0999 V2000
   -4.3617   -1.1041    1.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7962   -1.3798    0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0873   -0.1662    0.0771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9300    0.2323    0.9988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4171    1.5187    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5392    1.0844   -0.8567 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8300    1.0494   -0.3435 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9149    1.2753   -1.2276 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9185    1.8389   -2.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0799    0.8134   -0.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    1.1333   -0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3903    0.5621    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0048   -0.3765    1.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6676   -0.6956    1.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6834   -0.1333    0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2461   -0.2739    0.2856 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8082   -1.4450   -0.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6971   -1.2840   -0.4577 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9160   -0.8682    0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429   -0.4397    1.5161 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9568   -1.4975    2.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0828   -0.1585   -1.3238 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5482   -0.1719   -1.3128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0703    0.8442   -2.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8293   -0.0824    1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1008   -1.8553    2.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5561   -1.1000    2.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -2.2942    0.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6703   -1.5362   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8037    0.7046    0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3366    0.4370    1.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8611    2.1394    1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432    2.0946   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6182    1.8185   -1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9630    1.7981    0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972    2.9544   -2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600    1.4176   -3.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8710    1.6752   -3.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7649    1.8799   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4323    0.8451    0.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7701   -0.8318    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4236   -1.4491    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1504   -1.3625   -1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0899   -2.3643   -0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2440   -2.1657   -0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2864   -1.7028    1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3587    0.4848    2.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3255   -1.2057    3.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8375   -1.1490   -1.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3237    0.4918   -3.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 23  3  1  0
 19  4  1  0
 22  6  1  0
 16  7  1  0
 15 10  1  0
 20 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  6
  4 31  1  1
  5 32  1  0
  5 33  1  0
  6 34  1  6
  7 35  1  1
  9 36  1  0
  9 37  1  0
  9 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  6
 19 46  1  0
 20 47  1  1
 21 48  1  0
 23 49  1  6
 24 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      22.022 -18.249   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.022 -19.789   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.355 -20.559   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.689 -19.789   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.689 -18.249   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.355 -17.479   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      26.154 -20.265   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      27.059 -19.019   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.154 -17.773   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.590 -18.858   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      29.217 -17.451   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      28.312 -16.205   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.780 -16.366   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.997 -19.484   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.624 -18.077   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.097 -17.825   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.690 -17.199   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.637 -17.825   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.186 -14.144   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      32.068 -16.422   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      26.231 -14.154   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.154 -21.805   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      25.083 -13.087   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      34.427 -19.193   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8   22                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5   13   21                                             
CONECT   10    8   11   14                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12    9                                                       
CONECT   14   10   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   11   20                                                  
CONECT   18   16   24                                                       
CONECT   19   12   15   21                                                  
CONECT   20   17                                                            
CONECT   21    9   19   23                                                  
CONECT   22    7                                                            
CONECT   23   21                                                            
CONECT   24   18                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

COMPND    HMDB0015495
HETATM    1  C1  UNL     1      -4.362  -1.104   1.915  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.796  -1.380   0.516  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.087  -0.166   0.077  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.930   0.232   0.999  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.417   1.519   0.331  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.539   1.084  -0.857  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.830   1.049  -0.343  1.00  0.00           C  
HETATM    8  N1  UNL     1       1.915   1.275  -1.228  1.00  0.00           N  
HETATM    9  C8  UNL     1       1.919   1.839  -2.543  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.080   0.813  -0.533  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.421   1.133  -0.632  1.00  0.00           C  
HETATM   12  C11 UNL     1       5.390   0.562   0.152  1.00  0.00           C  
HETATM   13  C12 UNL     1       5.005  -0.377   1.083  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.668  -0.696   1.182  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.683  -0.133   0.404  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.246  -0.274   0.286  1.00  0.00           C  
HETATM   17  C16 UNL     1       0.808  -1.445  -0.564  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.697  -1.284  -0.458  1.00  0.00           C  
HETATM   19  C18 UNL     1      -0.916  -0.868   0.956  1.00  0.00           C  
HETATM   20  C19 UNL     1       0.443  -0.440   1.516  1.00  0.00           C  
HETATM   21  O1  UNL     1       0.957  -1.498   2.264  1.00  0.00           O  
HETATM   22  N2  UNL     1      -1.083  -0.159  -1.324  1.00  0.00           N  
HETATM   23  C20 UNL     1      -2.548  -0.172  -1.313  1.00  0.00           C  
HETATM   24  O2  UNL     1      -3.070   0.844  -2.115  1.00  0.00           O  
HETATM   25  H1  UNL     1      -4.829  -0.082   1.929  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.101  -1.855   2.216  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.556  -1.100   2.677  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.215  -2.294   0.568  1.00  0.00           H  
HETATM   29  H5  UNL     1      -4.670  -1.536  -0.138  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.804   0.705   0.144  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.337   0.437   1.999  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.861   2.139   1.038  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.243   2.095  -0.111  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.618   1.818  -1.684  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.963   1.798   0.497  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.797   2.954  -2.414  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.060   1.418  -3.107  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.871   1.675  -3.087  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.765   1.880  -1.366  1.00  0.00           H  
HETATM   40  H16 UNL     1       6.432   0.845   0.038  1.00  0.00           H  
HETATM   41  H17 UNL     1       5.770  -0.832   1.707  1.00  0.00           H  
HETATM   42  H18 UNL     1       3.424  -1.449   1.941  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.150  -1.362  -1.609  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.090  -2.364  -0.053  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.244  -2.166  -0.789  1.00  0.00           H  
HETATM   46  H22 UNL     1      -1.286  -1.703   1.544  1.00  0.00           H  
HETATM   47  H23 UNL     1       0.359   0.485   2.107  1.00  0.00           H  
HETATM   48  H24 UNL     1       1.325  -1.206   3.123  1.00  0.00           H  
HETATM   49  H25 UNL     1      -2.837  -1.149  -1.783  1.00  0.00           H  
HETATM   50  H26 UNL     1      -3.324   0.492  -3.023  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   23   30
CONECT    4    5   19   31
CONECT    5    6   32   33
CONECT    6    7   22   34
CONECT    7    8   16   35
CONECT    8    9   10
CONECT    9   36   37   38
CONECT   10   11   11   15
CONECT   11   12   39
CONECT   12   13   13   40
CONECT   13   14   41
CONECT   14   15   15   42
CONECT   15   16
CONECT   16   17   20
CONECT   17   18   43   44
CONECT   18   19   22   45
CONECT   19   20   46
CONECT   20   21   47
CONECT   21   48
CONECT   22   23
CONECT   23   24   49
CONECT   24   50
END

HMDB0015495
     RDKit          3D
Ajmaline
 50 55  0  0  0  0  0  0  0  0999 V2000
   -4.3617   -1.1041    1.9153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7962   -1.3798    0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0873   -0.1662    0.0771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9300    0.2323    0.9988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4171    1.5187    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5392    1.0844   -0.8567 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8300    1.0494   -0.3435 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9149    1.2753   -1.2276 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9185    1.8389   -2.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0799    0.8134   -0.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    1.1333   -0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3903    0.5621    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0048   -0.3765    1.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6676   -0.6956    1.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6834   -0.1333    0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2461   -0.2739    0.2856 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8082   -1.4450   -0.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6971   -1.2840   -0.4577 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9160   -0.8682    0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429   -0.4397    1.5161 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9568   -1.4975    2.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0828   -0.1585   -1.3238 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5482   -0.1719   -1.3128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0703    0.8442   -2.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8293   -0.0824    1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1008   -1.8553    2.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5561   -1.1000    2.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -2.2942    0.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6703   -1.5362   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8037    0.7046    0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3366    0.4370    1.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8611    2.1394    1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432    2.0946   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6182    1.8185   -1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9630    1.7981    0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972    2.9544   -2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600    1.4176   -3.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8710    1.6752   -3.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7649    1.8799   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4323    0.8451    0.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7701   -0.8318    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4236   -1.4491    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1504   -1.3625   -1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0899   -2.3643   -0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2440   -2.1657   -0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2864   -1.7028    1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3587    0.4848    2.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3255   -1.2057    3.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8375   -1.1490   -1.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3237    0.4918   -3.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 16 15  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 23  3  1  0
 19  4  1  0
 22  6  1  0
 16  7  1  0
 15 10  1  0
 20 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  6
  4 31  1  1
  5 32  1  0
  5 33  1  0
  6 34  1  6
  7 35  1  1
  9 36  1  0
  9 37  1  0
  9 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  6
 19 46  1  0
 20 47  1  1
 21 48  1  0
 23 49  1  6
 24 50  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+)-Ajmaline	ChEBI
(5AR,6S,8S,10S,11S,11as,12ar,13R)-5-methyl-5a,6,8,9,10,11,11a,12-octahydro-5H-6,10:11,12a-dimethanoindolo[3,2-b]quinolizine-8,13-diol	ChEBI
Ajimalin	Kegg
Ajmalin	HMDB

Chemical Formula

C₂₀H₂₆N₂O₂

Average Molecular Weight

326.4326

Monoisotopic Molecular Weight

326.199428086

IUPAC Name

(1R,9R,10S,12R,13S,14R,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-14,18-diol

Traditional Name

ajmaline

CAS Registry Number

4360-12-7

SMILES

CC[C@H]1[C@@H]2C[C@H]3[C@@H]4N(C)C5=CC=CC=C5[C@]44C[C@@H](C2[C@H]4O)N3[C@@H]1O

InChI Identifier

InChI=1S/C20H26N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3/t10-,11-,14-,15-,16?,17-,18+,19+,20+/m0/s1

InChI Key

CJDRUOGAGYHKKD-HEFSZTOGSA-N

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
Beta-carboline
Pyridoindole
Quinolizidine
Indole or derivatives
Dialkylarylamine
Quinuclidine
Tertiary aliphatic/aromatic amine
Azepane
Aralkylamine
Benzenoid
Piperidine
Cyclic alcohol
Secondary alcohol
Tertiary amine
Hemiaminal
Organoheterocyclic compound
Azacycle
Alkanolamine
Alcohol
Organopnictogen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hemiaminal (CHEBI:28462 )
monoterpenoid indole alkaloid (CHEBI:28462 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0015495)

Biofluid or Excreta

Blood (HMDB: HMDB0015495)
Urine (HMDB: HMDB0015495)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015495)
Membrane (HMDB: HMDB0015495)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0015495)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.09 g/L	Not Available
LogP	1.81	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.09 g/L	ALOGPS
logP	1.72	ALOGPS
logP	1.85	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	13.28	ChemAxon
pKa (Strongest Basic)	7.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.94 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.57 m³·mol⁻¹	ChemAxon
Polarizability	36.75 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	174.934	31661259
DarkChem	[M-H]-	170.152	31661259
DeepCCS	[M-2H]-	215.165	30932474
DeepCCS	[M+Na]+	189.66	30932474
AllCCS	[M+H]+	182.5	32859911
AllCCS	[M+H-H2O]+	179.5	32859911
AllCCS	[M+NH4]+	185.3	32859911
AllCCS	[M+Na]+	186.1	32859911
AllCCS	[M-H]-	188.7	32859911
AllCCS	[M+Na-2H]-	188.4	32859911
AllCCS	[M+HCOO]-	188.3	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ajmaline,1TMS,isomer #1	CC[C@H]1[C@@H]2C[C@H]3[C@@H]4N(C)C5=CC=CC=C5[C@]45C[C@@H](C2[C@H]5O[Si](C)(C)C)N3[C@@H]1O	2617.2	Semi standard non polar	33892256
Ajmaline,1TMS,isomer #2	CC[C@H]1[C@@H]2C[C@H]3[C@@H]4N(C)C5=CC=CC=C5[C@]45C[C@@H](C2[C@H]5O)N3[C@@H]1O[Si](C)(C)C	2628.0	Semi standard non polar	33892256
Ajmaline,2TMS,isomer #1	CC[C@H]1[C@@H]2C[C@H]3[C@@H]4N(C)C5=CC=CC=C5[C@]45C[C@@H](C2[C@H]5O[Si](C)(C)C)N3[C@@H]1O[Si](C)(C)C	2611.8	Semi standard non polar	33892256
Ajmaline,1TBDMS,isomer #1	CC[C@H]1[C@@H]2C[C@H]3[C@@H]4N(C)C5=CC=CC=C5[C@]45C[C@@H](C2[C@H]5O[Si](C)(C)C(C)(C)C)N3[C@@H]1O	2849.8	Semi standard non polar	33892256
Ajmaline,1TBDMS,isomer #2	CC[C@H]1[C@@H]2C[C@H]3[C@@H]4N(C)C5=CC=CC=C5[C@]45C[C@@H](C2[C@H]5O)N3[C@@H]1O[Si](C)(C)C(C)(C)C	2827.7	Semi standard non polar	33892256
Ajmaline,2TBDMS,isomer #1	CC[C@H]1[C@@H]2C[C@H]3[C@@H]4N(C)C5=CC=CC=C5[C@]45C[C@@H](C2[C@H]5O[Si](C)(C)C(C)(C)C)N3[C@@H]1O[Si](C)(C)C(C)(C)C	3018.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ajmaline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bta-2498000000-49bdb2b520b940e4152b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ajmaline GC-MS (2 TMS) - 70eV, Positive	splash10-0a59-9006700000-c3e3a75dc9384667f4a8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ajmaline GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ajmaline GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ajmaline GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ajmaline GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ajmaline GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ajmaline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ajmaline GC-MS ("Ajmaline,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajmaline 10V, Positive-QTOF	splash10-0a6r-0009000000-852cc00f822b12dde86f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajmaline 20V, Positive-QTOF	splash10-0a6r-0029000000-f1807eeec4b4f036d14f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajmaline 40V, Positive-QTOF	splash10-0a5c-1492000000-fc9be42e8caaa18f3f1d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajmaline 10V, Negative-QTOF	splash10-004i-0009000000-622c9342ca8dd4c7306c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajmaline 20V, Negative-QTOF	splash10-004i-0029000000-b0778df2272e5a83567c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajmaline 40V, Negative-QTOF	splash10-055b-0092000000-b4a357ef59beb58eff9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajmaline 10V, Positive-QTOF	splash10-004i-0009000000-dae1999fa32e1d569c50	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajmaline 20V, Positive-QTOF	splash10-004i-0009000000-26633a00421c4e37223e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajmaline 40V, Positive-QTOF	splash10-002b-0289000000-81cc4c52227dacb33909	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajmaline 10V, Negative-QTOF	splash10-004i-0009000000-dac436f1ca5194242739	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajmaline 20V, Negative-QTOF	splash10-004i-0009000000-dac436f1ca5194242739	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ajmaline 40V, Negative-QTOF	splash10-00di-0049000000-faf20d5a5170e947fc9b	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01426	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01426	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01426

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ajmaline

METLIN ID

Not Available

PubChem Compound

441080

PDB ID

Not Available

ChEBI ID

28462

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Brugada J, Brugada P, Brugada R: The ajmaline challenge in Brugada syndrome: a useful tool or misleading information? Eur Heart J. 2003 Jun;24(12):1085-6. [PubMed:12804922 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Sodium channel protein type 5 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:: SCN5A
Uniprot ID:: Q14524
Molecular weight:: 226937.5

References

Barajas-Martinez HM, Hu D, Cordeiro JM, Wu Y, Kovacs RJ, Meltser H, Kui H, Elena B, Brugada R, Antzelevitch C, Dumaine R: Lidocaine-induced Brugada syndrome phenotype linked to a novel double mutation in the cardiac sodium channel. Circ Res. 2008 Aug 15;103(4):396-404. doi: 10.1161/CIRCRESAHA.108.172619. Epub 2008 Jul 3. [PubMed:18599870 ]
Khodorov BI, Zaborovskaya LD: Blockade of sodium and potassium channels in the node of Ranvier by ajmaline and N-propyl ajmaline. Gen Physiol Biophys. 1983 Aug;2(4):233-68. [PubMed:6088360 ]
Hermida JS, Dassonvalle E, Six I, Amant C, Coviaux F, Clerc J, Herent D, Hermida A, Rochette J, Jarry G: Prospective evaluation of the familial prevalence of the brugada syndrome. Am J Cardiol. 2010 Dec 15;106(12):1758-62. doi: 10.1016/j.amjcard.2010.07.049. [PubMed:21126620 ]
Hoogendijk MG, Potse M, Vinet A, de Bakker JM, Coronel R: ST segment elevation by current-to-load mismatch: an experimental and computational study. Heart Rhythm. 2011 Jan;8(1):111-8. doi: 10.1016/j.hrthm.2010.09.066. Epub 2010 Oct 30. [PubMed:20870038 ]
Leoni AL, Gavillet B, Rougier JS, Marionneau C, Probst V, Le Scouarnec S, Schott JJ, Demolombe S, Bruneval P, Huang CL, Colledge WH, Grace AA, Le Marec H, Wilde AA, Mohler PJ, Escande D, Abriel H, Charpentier F: Variable Na(v)1.5 protein expression from the wild-type allele correlates with the penetrance of cardiac conduction disease in the Scn5a(+/-) mouse model. PLoS One. 2010 Feb 19;5(2):e9298. doi: 10.1371/journal.pone.0009298. [PubMed:20174578 ]
Hoogendijk MG, Potse M, Linnenbank AC, Verkerk AO, den Ruijter HM, van Amersfoorth SC, Klaver EC, Beekman L, Bezzina CR, Postema PG, Tan HL, Reimer AG, van der Wal AC, Ten Harkel AD, Dalinghaus M, Vinet A, Wilde AA, de Bakker JM, Coronel R: Mechanism of right precordial ST-segment elevation in structural heart disease: excitation failure by current-to-load mismatch. Heart Rhythm. 2010;7(2):238-48. doi: 10.1016/j.hrthm.2009.10.007. Epub 2009 Oct 12. [PubMed:20022821 ]

Showing metabocard for Ajmaline (HMDB0015495)

MOL for HMDB0015495 (Ajmaline)

3D MOL for HMDB0015495 (Ajmaline)

3D SDF for HMDB0015495 (Ajmaline)

3D-SDF for HMDB0015495 (Ajmaline)

PDB for HMDB0015495 (Ajmaline)

3D PDB for HMDB0015495 (Ajmaline)

SMILES for HMDB0015495 (Ajmaline)

INCHI for HMDB0015495 (Ajmaline)

Structure for HMDB0015495 (Ajmaline)

3D Structure for HMDB0015495 (Ajmaline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References