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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014837

Secondary Accession Numbers

HMDB14837

Metabolite Identification

Common Name

Nicergoline

Description

Nicergoline is only found in individuals that have used or taken this drug. It is an ergot derivative that has been used as a cerebral vasodilator and in peripheral vascular disease. It has been suggested to ameliorate cognitive deficits in cerebrovascular disease. [PubChem]Nicergoline acts by inhibiting the postsynaptic alpha(1)-adrenoceptors on vascular smooth muscle. This inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation. Therefore the mechanism of Nicergoline is to increase vascular circulation in the brain, thereby enhancing the transmission of nerve signals across the nerve fibres, which secrete acetylcholine as a neural transmitter.

Structure

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

699
  Mrv0541 02231214562D          

 32 36  0  0  1  0            999 V2000
    3.7918    4.1206    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.8506   -1.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885    1.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596    1.2249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2928   -0.0101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2679   -3.4061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.6998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5651   -1.2819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2796   -0.8694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8143   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8077   -0.0044    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9940   -1.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5651   -2.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5519    0.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2796   -2.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9940   -2.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917    0.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2928   -3.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0120    0.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8143   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6021   -2.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5519   -3.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8077   -3.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1362   -1.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6804   -4.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725    1.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3692    2.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821    2.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6532    2.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    3.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3629    4.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8536   -0.5438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 30  1  0  0  0  0
  8  2  1  6  0  0  0
  2 24  1  0  0  0  0
  3 17  1  0  0  0  0
  3 26  1  0  0  0  0
  4 26  2  0  0  0  0
  5  9  1  0  0  0  0
  5 14  1  0  0  0  0
  5 19  1  0  0  0  0
  6 18  1  0  0  0  0
  6 21  1  0  0  0  0
  6 25  1  0  0  0  0
  7 29  2  0  0  0  0
  7 31  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  9 12  1  0  0  0  0
  9 32  1  1  0  0  0
 10 11  1  0  0  0  0
 11 14  1  0  0  0  0
 11 17  1  1  0  0  0
 12 16  1  0  0  0  0
 13 15  2  0  0  0  0
 13 20  1  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 21  2  0  0  0  0
 18 22  2  0  0  0  0
 20 23  2  0  0  0  0
 22 23  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END

HMDB0014837
     RDKit          3D
Nicergoline
 57 61  0  0  0  0  0  0  0  0999 V2000
   -2.0306   -0.1288    3.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0633    0.1412    1.9077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1688    0.4048    0.9969 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1542   -0.7431    0.8980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8952   -0.5276    1.9230 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7964   -1.6440    2.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117   -2.2340    1.3700 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555   -2.9709    0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1652   -3.2229   -0.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4432   -3.5105   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7655   -3.2598   -0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7724   -3.7287   -1.0795 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634   -4.4828   -2.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -4.7988   -2.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7758   -5.8757   -4.0283 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.1431   -4.2827   -1.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6717    0.7429    1.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    1.8429    1.7542 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4186    3.0589    1.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4167    1.6720    0.9200 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2872    2.9095    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211    2.8315   -0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7185    3.6972   -1.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3325    3.0357   -2.2285 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0614    3.6287   -3.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1204    1.7270   -2.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4598    0.5341   -2.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0573   -0.6940   -2.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2951   -0.7974   -0.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657    0.3859   -0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3664    1.5759   -0.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1314   -0.2251    3.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6666   -1.1489    3.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6437    0.6830    3.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6644   -1.7042    1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2892   -0.7330   -0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479   -0.2673    2.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4775   -1.2740    3.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1588   -2.3988    2.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0068   -2.6552    0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2265   -4.8986   -2.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -4.4951   -1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5086    0.9224    2.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085    0.6747    0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2847    3.2310    0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722    3.9417    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5121    2.9892    1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0370    1.6545   -0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385    3.7950    0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8831    3.0821    1.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6965    4.7880   -1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7703    4.7157   -3.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8622    3.1247   -4.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1612    3.6462   -3.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0541    0.6114   -3.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3317   -1.6134   -2.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9821   -1.7324   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  5 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 20  3  1  0
 31 22  1  0
 30  3  1  0
 16 10  1  0
 31 26  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  1
  6 38  1  0
  6 39  1  0
 11 40  1  0
 13 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  6
 21 49  1  0
 21 50  1  0
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
M  END

699
  Mrv0541 02231214562D          

 32 36  0  0  1  0            999 V2000
    3.7918    4.1206    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.8506   -1.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885    1.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596    1.2249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2928   -0.0101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2679   -3.4061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.6998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5651   -1.2819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2796   -0.8694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8143   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8077   -0.0044    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9940   -1.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5651   -2.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5519    0.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2796   -2.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9940   -2.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917    0.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2928   -3.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0120    0.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8143   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6021   -2.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5519   -3.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8077   -3.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1362   -1.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6804   -4.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725    1.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3692    2.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821    2.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6532    2.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    3.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3629    4.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8536   -0.5438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 30  1  0  0  0  0
  8  2  1  6  0  0  0
  2 24  1  0  0  0  0
  3 17  1  0  0  0  0
  3 26  1  0  0  0  0
  4 26  2  0  0  0  0
  5  9  1  0  0  0  0
  5 14  1  0  0  0  0
  5 19  1  0  0  0  0
  6 18  1  0  0  0  0
  6 21  1  0  0  0  0
  6 25  1  0  0  0  0
  7 29  2  0  0  0  0
  7 31  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  9 12  1  0  0  0  0
  9 32  1  1  0  0  0
 10 11  1  0  0  0  0
 11 14  1  0  0  0  0
 11 17  1  1  0  0  0
 12 16  1  0  0  0  0
 13 15  2  0  0  0  0
 13 20  1  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 21  2  0  0  0  0
 18 22  2  0  0  0  0
 20 23  2  0  0  0  0
 22 23  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014837

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC3=CN(C)C4=CC=CC(=C34)[C@]1(C[C@@H](COC(=O)C1=CC(Br)=CN=C1)CN2C)OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H26BrN3O3/c1-27-13-17-8-21-24(30-3,19-5-4-6-20(27)22(17)19)9-15(12-28(21)2)14-31-23(29)16-7-18(25)11-26-10-16/h4-7,10-11,13,15,21H,8-9,12,14H2,1-3H3/t15-,21-,24+/m1/s1

> <INCHI_KEY>
YSEXMKHXIOCEJA-FVFQAYNVSA-N

> <FORMULA>
C24H26BrN3O3

> <MOLECULAR_WEIGHT>
484.386

> <EXACT_MASS>
483.11575436

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
48.08314320179508

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
3.6953249436666655

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.137752026763765

> <JCHEM_POLAR_SURFACE_AREA>
56.59

> <JCHEM_REFRACTIVITY>
123.29739999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nicergoline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014837
     RDKit          3D
Nicergoline
 57 61  0  0  0  0  0  0  0  0999 V2000
   -2.0306   -0.1288    3.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0633    0.1412    1.9077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1688    0.4048    0.9969 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1542   -0.7431    0.8980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8952   -0.5276    1.9230 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7964   -1.6440    2.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117   -2.2340    1.3700 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555   -2.9709    0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1652   -3.2229   -0.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4432   -3.5105   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7655   -3.2598   -0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7724   -3.7287   -1.0795 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634   -4.4828   -2.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -4.7988   -2.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7758   -5.8757   -4.0283 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.1431   -4.2827   -1.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6717    0.7429    1.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    1.8429    1.7542 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4186    3.0589    1.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4167    1.6720    0.9200 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2872    2.9095    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211    2.8315   -0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7185    3.6972   -1.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3325    3.0357   -2.2285 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0614    3.6287   -3.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1204    1.7270   -2.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4598    0.5341   -2.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0573   -0.6940   -2.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2951   -0.7974   -0.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657    0.3859   -0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3664    1.5759   -0.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1314   -0.2251    3.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6666   -1.1489    3.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6437    0.6830    3.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6644   -1.7042    1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2892   -0.7330   -0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479   -0.2673    2.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4775   -1.2740    3.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1588   -2.3988    2.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0068   -2.6552    0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2265   -4.8986   -2.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -4.4951   -1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5086    0.9224    2.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085    0.6747    0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2847    3.2310    0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722    3.9417    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5121    2.9892    1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0370    1.6545   -0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385    3.7950    0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8831    3.0821    1.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6965    4.7880   -1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7703    4.7157   -3.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8622    3.1247   -4.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1612    3.6462   -3.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0541    0.6114   -3.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3317   -1.6134   -2.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9821   -1.7324   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  5 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 20  3  1  0
 31 22  1  0
 30  3  1  0
 16 10  1  0
 31 26  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  1
  6 38  1  0
  6 39  1  0
 11 40  1  0
 13 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  6
 21 49  1  0
 21 50  1  0
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 699                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Br   UNK     0       7.078   7.692   0.000  0.00  0.00          Br+0
HETATM    2  O   UNK     0       7.188  -3.163   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.765   2.297   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.098   2.286   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.880  -0.019   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      11.700  -6.358   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       3.080   6.906   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       8.522  -2.393   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.855  -1.623   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.120  -1.612   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.108  -0.008   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.189  -2.393   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.522  -3.933   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.497   0.794   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.855  -4.703   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.189  -3.933   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.771   0.757   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.880  -6.307   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.222   0.736   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.120  -4.713   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.324  -4.960   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.497  -7.119   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.108  -6.317   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.854  -2.393   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.470  -7.692   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.429   3.062   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.423   4.602   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.753   5.377   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.086   5.366   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.747   6.917   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.411   7.682   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      10.927  -1.015   0.000  0.00  0.00           H+0
CONECT    1   30                                                            
CONECT    2    8   24                                                       
CONECT    3   17   26                                                       
CONECT    4   26                                                            
CONECT    5    9   14   19                                                  
CONECT    6   18   21   25                                                  
CONECT    7   29   31                                                       
CONECT    8    2    9   10   13                                             
CONECT    9    5    8   12   32                                             
CONECT   10    8   11                                                       
CONECT   11   10   14   17                                                  
CONECT   12    9   16                                                       
CONECT   13    8   15   20                                                  
CONECT   14    5   11                                                       
CONECT   15   13   16   18                                                  
CONECT   16   12   15   21                                                  
CONECT   17    3   11                                                       
CONECT   18    6   15   22                                                  
CONECT   19    5                                                            
CONECT   20   13   23                                                       
CONECT   21    6   16                                                       
CONECT   22   18   23                                                       
CONECT   23   20   22                                                       
CONECT   24    2                                                            
CONECT   25    6                                                            
CONECT   26    3    4   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   30                                                       
CONECT   29    7   27                                                       
CONECT   30    1   28   31                                                  
CONECT   31    7   30                                                       
CONECT   32    9                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

COMPND    HMDB0014837
HETATM    1  C1  UNL     1      -2.031  -0.129   3.183  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.063   0.141   1.908  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.169   0.405   0.997  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.154  -0.743   0.898  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.895  -0.528   1.923  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.796  -1.644   2.279  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.612  -2.234   1.370  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.356  -2.971   0.279  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.165  -3.223  -0.033  1.00  0.00           O  
HETATM   10  C7  UNL     1       3.443  -3.510  -0.590  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.766  -3.260  -0.326  1.00  0.00           C  
HETATM   12  N1  UNL     1       5.772  -3.729  -1.080  1.00  0.00           N  
HETATM   13  C9  UNL     1       5.463  -4.483  -2.147  1.00  0.00           C  
HETATM   14  C10 UNL     1       4.154  -4.799  -2.505  1.00  0.00           C  
HETATM   15 BR1  UNL     1       3.776  -5.876  -4.028  1.00  0.00          BR  
HETATM   16  C11 UNL     1       3.143  -4.283  -1.684  1.00  0.00           C  
HETATM   17  C12 UNL     1       1.672   0.743   1.553  1.00  0.00           C  
HETATM   18  N2  UNL     1       0.722   1.843   1.754  1.00  0.00           N  
HETATM   19  C13 UNL     1       1.419   3.059   1.322  1.00  0.00           C  
HETATM   20  C14 UNL     1      -0.417   1.672   0.920  1.00  0.00           C  
HETATM   21  C15 UNL     1      -1.287   2.909   0.866  1.00  0.00           C  
HETATM   22  C16 UNL     1      -2.121   2.832  -0.377  1.00  0.00           C  
HETATM   23  C17 UNL     1      -2.718   3.697  -1.228  1.00  0.00           C  
HETATM   24  N3  UNL     1      -3.333   3.036  -2.229  1.00  0.00           N  
HETATM   25  C18 UNL     1      -4.061   3.629  -3.308  1.00  0.00           C  
HETATM   26  C19 UNL     1      -3.120   1.727  -2.008  1.00  0.00           C  
HETATM   27  C20 UNL     1      -3.460   0.534  -2.635  1.00  0.00           C  
HETATM   28  C21 UNL     1      -3.057  -0.694  -2.118  1.00  0.00           C  
HETATM   29  C22 UNL     1      -2.295  -0.797  -0.946  1.00  0.00           C  
HETATM   30  C23 UNL     1      -1.966   0.386  -0.333  1.00  0.00           C  
HETATM   31  C24 UNL     1      -2.366   1.576  -0.855  1.00  0.00           C  
HETATM   32  H1  UNL     1      -3.131  -0.225   3.528  1.00  0.00           H  
HETATM   33  H2  UNL     1      -1.667  -1.149   3.492  1.00  0.00           H  
HETATM   34  H3  UNL     1      -1.644   0.683   3.831  1.00  0.00           H  
HETATM   35  H4  UNL     1      -0.664  -1.704   1.134  1.00  0.00           H  
HETATM   36  H5  UNL     1       0.289  -0.733  -0.143  1.00  0.00           H  
HETATM   37  H6  UNL     1       0.348  -0.267   2.898  1.00  0.00           H  
HETATM   38  H7  UNL     1       2.478  -1.274   3.128  1.00  0.00           H  
HETATM   39  H8  UNL     1       1.159  -2.399   2.853  1.00  0.00           H  
HETATM   40  H9  UNL     1       5.007  -2.655   0.529  1.00  0.00           H  
HETATM   41  H10 UNL     1       6.227  -4.899  -2.803  1.00  0.00           H  
HETATM   42  H11 UNL     1       2.121  -4.495  -1.916  1.00  0.00           H  
HETATM   43  H12 UNL     1       2.509   0.922   2.242  1.00  0.00           H  
HETATM   44  H13 UNL     1       1.908   0.675   0.492  1.00  0.00           H  
HETATM   45  H14 UNL     1       1.285   3.231   0.237  1.00  0.00           H  
HETATM   46  H15 UNL     1       1.072   3.942   1.920  1.00  0.00           H  
HETATM   47  H16 UNL     1       2.512   2.989   1.514  1.00  0.00           H  
HETATM   48  H17 UNL     1       0.037   1.654  -0.140  1.00  0.00           H  
HETATM   49  H18 UNL     1      -0.639   3.795   0.739  1.00  0.00           H  
HETATM   50  H19 UNL     1      -1.883   3.082   1.780  1.00  0.00           H  
HETATM   51  H20 UNL     1      -2.697   4.788  -1.104  1.00  0.00           H  
HETATM   52  H21 UNL     1      -3.770   4.716  -3.375  1.00  0.00           H  
HETATM   53  H22 UNL     1      -3.862   3.125  -4.280  1.00  0.00           H  
HETATM   54  H23 UNL     1      -5.161   3.646  -3.142  1.00  0.00           H  
HETATM   55  H24 UNL     1      -4.054   0.611  -3.548  1.00  0.00           H  
HETATM   56  H25 UNL     1      -3.332  -1.613  -2.624  1.00  0.00           H  
HETATM   57  H26 UNL     1      -1.982  -1.732  -0.542  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3
CONECT    3    4   20   30
CONECT    4    5   35   36
CONECT    5    6   17   37
CONECT    6    7   38   39
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   11   16
CONECT   11   12   40
CONECT   12   13   13
CONECT   13   14   41
CONECT   14   15   16   16
CONECT   16   42
CONECT   17   18   43   44
CONECT   18   19   20
CONECT   19   45   46   47
CONECT   20   21   48
CONECT   21   22   49   50
CONECT   22   23   23   31
CONECT   23   24   51
CONECT   24   25   26
CONECT   25   52   53   54
CONECT   26   27   27   31
CONECT   27   28   55
CONECT   28   29   29   56
CONECT   29   30   57
CONECT   30   31   31
END

HMDB0014837
     RDKit          3D
Nicergoline
 57 61  0  0  0  0  0  0  0  0999 V2000
   -2.0306   -0.1288    3.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0633    0.1412    1.9077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1688    0.4048    0.9969 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1542   -0.7431    0.8980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8952   -0.5276    1.9230 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7964   -1.6440    2.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117   -2.2340    1.3700 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555   -2.9709    0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1652   -3.2229   -0.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4432   -3.5105   -0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7655   -3.2598   -0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7724   -3.7287   -1.0795 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4634   -4.4828   -2.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -4.7988   -2.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7758   -5.8757   -4.0283 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.1431   -4.2827   -1.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6717    0.7429    1.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    1.8429    1.7542 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4186    3.0589    1.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4167    1.6720    0.9200 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2872    2.9095    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1211    2.8315   -0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7185    3.6972   -1.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3325    3.0357   -2.2285 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0614    3.6287   -3.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1204    1.7270   -2.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4598    0.5341   -2.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0573   -0.6940   -2.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2951   -0.7974   -0.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657    0.3859   -0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3664    1.5759   -0.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1314   -0.2251    3.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6666   -1.1489    3.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6437    0.6830    3.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6644   -1.7042    1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2892   -0.7330   -0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479   -0.2673    2.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4775   -1.2740    3.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1588   -2.3988    2.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0068   -2.6552    0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2265   -4.8986   -2.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -4.4951   -1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5086    0.9224    2.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085    0.6747    0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2847    3.2310    0.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722    3.9417    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5121    2.9892    1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0370    1.6545   -0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6385    3.7950    0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8831    3.0821    1.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6965    4.7880   -1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7703    4.7157   -3.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8622    3.1247   -4.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1612    3.6462   -3.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0541    0.6114   -3.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3317   -1.6134   -2.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9821   -1.7324   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
  5 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 20  3  1  0
 31 22  1  0
 30  3  1  0
 16 10  1  0
 31 26  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  1
  6 38  1  0
  6 39  1  0
 11 40  1  0
 13 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  6
 21 49  1  0
 21 50  1  0
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Sermion	Kegg
Circo-maren	HMDB
Dexcel brand OF nicergoline	HMDB
Nicergolin atid	HMDB
Nicergolin lindo	HMDB
Nicergolin-neuraxpharm	HMDB
Nicergoline hexal brand	HMDB
Nicerium	HMDB
Nicotergoline	HMDB
Pfizer brand OF nicergoline	HMDB
Teva brand OF nicergoline	HMDB
CT Arzneimittel brand OF nicergoline	HMDB
Neuraxpharm brand OF nicergoline	HMDB
Ratiopharm brand OF nicergoline	HMDB
Circo maren	HMDB
Fisifax	HMDB
Hormosan brand OF nicergoline	HMDB
Nicergobeta	HMDB
Nicergolin neuraxpharm	HMDB
Nicergolin-ratiopharm	HMDB
Nicergoline pfizer brand	HMDB
Nicergoline teva brand	HMDB
Reig jofre brand OF nicergoline	HMDB
Aventis brand OF nicergoline	HMDB
F.I. 6714	HMDB
Hexal brand OF nicergoline	HMDB
Lindopharm brand OF nicergoline	HMDB
Nicergolin-teva	HMDB
Betapharm brand OF nicergoline	HMDB
Kenfarma brand OF nicergoline	HMDB
Krewel brand OF nicergoline	HMDB
Nicergolin teva	HMDB
Nicergolin ratiopharm	HMDB
Nimergoline	HMDB
CT-Arzneimittel brand OF nicergoline	HMDB
Ergobel	HMDB
Nicergolin von CT	HMDB
Von CT, nicergolin	HMDB

Chemical Formula

C₂₄H₂₆BrN₃O₃

Average Molecular Weight

484.386

Monoisotopic Molecular Weight

483.11575436

IUPAC Name

[(2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate

Traditional Name

nicergoline

CAS Registry Number

27848-84-6

SMILES

[H][C@@]12CC3=CN(C)C4=CC=CC(=C34)[C@]1(C[C@@H](COC(=O)C1=CC(Br)=CN=C1)CN2C)OC

InChI Identifier

InChI=1S/C24H26BrN3O3/c1-27-13-17-8-21-24(30-3,19-5-4-6-20(27)22(17)19)9-15(12-28(21)2)14-31-23(29)16-7-18(25)11-26-10-16/h4-7,10-11,13,15,21H,8-9,12,14H2,1-3H3/t15-,21-,24+/m1/s1

InChI Key

YSEXMKHXIOCEJA-FVFQAYNVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Indoloquinolines

Direct Parent

Indoloquinolines

Alternative Parents

Substituents

Ergoline skeleton
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
N-alkylindole
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Pyridine carboxylic acid
Alkaloid or derivatives
Pyridine carboxylic acid or derivatives
Aralkylamine
Aryl bromide
Aryl halide
N-methylpyrrole
Piperidine
Benzenoid
Pyridine
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Dialkyl ether
Ether
Amine
Organopnictogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organohalogen compound
Organic nitrogen compound
Organobromide
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014837)

Source

Exogenous

Exogenous (HMDB: HMDB0014837)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.013 g/L	Not Available
LogP	3.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	213.815	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001017

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3.99	ALOGPS
logP	3.7	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	8.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	56.59 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	123.3 m³·mol⁻¹	ChemAxon
Polarizability	48.08 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M-2H]-	228.913	30932474
DeepCCS	[M+Na]+	204.336	30932474
AllCCS	[M+H]+	208.9	32859911
AllCCS	[M+H-H2O]+	206.9	32859911
AllCCS	[M+NH4]+	210.8	32859911
AllCCS	[M+Na]+	211.3	32859911
AllCCS	[M-H]-	207.1	32859911
AllCCS	[M+Na-2H]-	207.8	32859911
AllCCS	[M+HCOO]-	208.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.55 minutes	32390414
Predicted by Siyang on May 30, 2022	11.631 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.97 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	64.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2169.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	194.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	186.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	107.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	412.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	442.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	370.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	960.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	285.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1296.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	284.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	351.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	317.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	269.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	20.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nicergoline	[H][C@@]12CC3=CN(C)C4=CC=CC(=C34)[C@]1(C[C@@H](COC(=O)C1=CC(Br)=CN=C1)CN2C)OC	4605.5	Standard polar	33892256
Nicergoline	[H][C@@]12CC3=CN(C)C4=CC=CC(=C34)[C@]1(C[C@@H](COC(=O)C1=CC(Br)=CN=C1)CN2C)OC	3418.3	Standard non polar	33892256
Nicergoline	[H][C@@]12CC3=CN(C)C4=CC=CC(=C34)[C@]1(C[C@@H](COC(=O)C1=CC(Br)=CN=C1)CN2C)OC	3739.0	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 - Nicergoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-01oy-0490000000-9946900f54448caef05c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicergoline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicergoline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Nicergoline 10V, Positive-QTOF	splash10-001i-0070900000-31a0fe890dfcef178a8d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicergoline 20V, Positive-QTOF	splash10-001i-0090200000-e7257eb7542660c9b4c7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicergoline 40V, Positive-QTOF	splash10-0pc0-2390000000-90dd1884dd9a2c36f452	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicergoline 10V, Negative-QTOF	splash10-001i-0110900000-1589cacb0deaf8363131	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicergoline 20V, Negative-QTOF	splash10-0532-0920500000-513d6a319962dbf7cbf3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicergoline 40V, Negative-QTOF	splash10-0a4j-0920000000-330babe951e9ccb2384a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicergoline 10V, Positive-QTOF	splash10-0udi-0000900000-2649cd14eb52b3a4655b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicergoline 20V, Positive-QTOF	splash10-001i-0000900000-a0efe44d5c8b6301ef53	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicergoline 40V, Positive-QTOF	splash10-0udi-0391000000-906dc143d70f8ce61d0e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicergoline 10V, Negative-QTOF	splash10-001i-0000900000-b7c2f66e57ef37412e1a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicergoline 20V, Negative-QTOF	splash10-003r-4100900000-fe5f17d8fb6e1a206cbd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicergoline 40V, Negative-QTOF	splash10-0a6r-2900100000-a189dad93ea9944c264f	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB00699	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00699	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00699

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31373

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nicergoline

METLIN ID

Not Available

PubChem Compound

34040

PDB ID

Not Available

ChEBI ID

Not Available

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

Winblad B, Fioravanti M, Dolezal T, Logina I, Milanov IG, Popescu DC, Solomon A: Therapeutic use of nicergoline. Clin Drug Investig. 2008;28(9):533-52. [PubMed:18666801 ]

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. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Alvarez-Guerra M, Bertholom N, Garay RP: Selective blockade by nicergoline of vascular responses elicited by stimulation of alpha 1A-adrenoceptor subtype in the rat. Fundam Clin Pharmacol. 1999;13(1):50-8. [PubMed:10027088 ]

Showing metabocard for Nicergoline (HMDB0014837)

MOL for HMDB0014837 (Nicergoline)

3D MOL for HMDB0014837 (Nicergoline)

3D SDF for HMDB0014837 (Nicergoline)

3D-SDF for HMDB0014837 (Nicergoline)

PDB for HMDB0014837 (Nicergoline)

3D PDB for HMDB0014837 (Nicergoline)

SMILES for HMDB0014837 (Nicergoline)

INCHI for HMDB0014837 (Nicergoline)

Structure for HMDB0014837 (Nicergoline)

3D Structure for HMDB0014837 (Nicergoline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References