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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:19:52 UTC

HMDB ID

HMDB0001091

Secondary Accession Numbers

HMDB01091

Metabolite Identification

Common Name

3-Hydroxyquinine

Description

3-Hydroxyquinine belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety. 3-Hydroxyquinine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxyquinine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-Hydroxyquinine.

Structure

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


  Mrv0541 02231218552D          

 27 30  0  0  1  0            999 V2000
   -0.7620   -1.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0448   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7654   -2.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723   -0.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0414   -0.0552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6689   -1.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723   -2.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -2.5274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895   -1.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6758    0.3552    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7551    0.3621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6654   -2.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895   -2.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9033   -0.8758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5206    0.8689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2448    0.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9033   -0.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5206    1.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    0.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758    1.4585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0792    2.0412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9929    1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7689    2.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585    2.6308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2758    3.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965   -0.4034    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586    1.8722    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  1  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
 14 17  1  0  0  0  0
 15 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 21 23  1  1  0  0  0
 21 24  1  0  0  0  0
 23 25  2  0  0  0  0
  8 12  2  0  0  0  0
  9 13  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 10 26  1  1  0  0  0
 20 27  1  1  0  0  0
M  END

HMDB0001091
     RDKit          3D
3-Hydroxyquinine
 49 52  0  0  0  0  0  0  0  0999 V2000
    5.5381    0.9636   -1.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4831    0.1916   -1.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1641    0.5993   -0.7964 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7809    1.8596   -1.2155 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109   -0.3782   -1.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6050   -1.0981   -0.0941 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517   -1.7571    0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -0.7633    1.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2767    0.6199    0.7135 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8888    0.9331    1.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0005   -0.2677    0.8952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3611    0.2675    0.5097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7579    1.0605    1.6181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991   -0.8670    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171   -2.1816    0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9578   -3.1918    0.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1682   -2.8573   -0.0503 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5178   -1.5714   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7886   -1.2859   -0.7755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1310    0.0309   -1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2239    1.0520   -0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5776    2.3643   -1.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8271    2.7664   -1.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9679    0.7214   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5858   -0.5754   -0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4468    1.9015   -0.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5199    0.7058   -1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5977   -0.7133   -1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0656    2.5911   -0.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5463   -1.1599   -1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2944    0.0963   -1.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3456   -2.2931   -0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501   -2.5304    1.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7040   -0.9827    1.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2781   -0.7628    2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0316    1.3464    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9914    1.0442    2.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4729    1.8654    0.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8987   -0.8593    1.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823    0.8976   -0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3320    0.5583    2.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376   -2.4331    0.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545   -4.2026    0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4640   -2.1136   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1250    0.2423   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2031    2.0693   -2.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5152    2.7964   -0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7504    3.8124   -1.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303    1.4883   -0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  2  0
  9  3  1  0
 25 14  1  0
 11  6  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  6
 10 37  1  0
 10 38  1  0
 11 39  1  1
 12 40  1  6
 13 41  1  0
 15 42  1  0
 16 43  1  0
 19 44  1  0
 20 45  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
M  END


  Mrv0541 02231218552D          

 27 30  0  0  1  0            999 V2000
   -0.7620   -1.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0448   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7654   -2.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723   -0.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0414   -0.0552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6689   -1.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723   -2.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -2.5274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895   -1.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6758    0.3552    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7551    0.3621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6654   -2.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895   -2.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9033   -0.8758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5206    0.8689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2448    0.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9033   -0.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5206    1.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    0.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758    1.4585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0792    2.0412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9929    1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7689    2.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585    2.6308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2758    3.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965   -0.4034    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586    1.8722    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  1  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
 14 17  1  0  0  0  0
 15 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 21 23  1  1  0  0  0
 21 24  1  0  0  0  0
 23 25  2  0  0  0  0
  8 12  2  0  0  0  0
  9 13  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 10 26  1  1  0  0  0
 20 27  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0001091

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18+,19-,20-/m1/s1

> <INCHI_KEY>
BSRUJCFCZKMFMB-ZNYHDOEXSA-N

> <FORMULA>
C20H24N2O3

> <MOLECULAR_WEIGHT>
340.4162

> <EXACT_MASS>
340.178692644

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.88782587536071

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R,6S)-3-ethenyl-6-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
1.6659791056666675

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.15810154930126

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.551720091556078

> <JCHEM_PKA_STRONGEST_BASIC>
8.62855835719494

> <JCHEM_POLAR_SURFACE_AREA>
65.82000000000001

> <JCHEM_REFRACTIVITY>
95.9137

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxyquinidine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001091
     RDKit          3D
3-Hydroxyquinine
 49 52  0  0  0  0  0  0  0  0999 V2000
    5.5381    0.9636   -1.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4831    0.1916   -1.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1641    0.5993   -0.7964 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7809    1.8596   -1.2155 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109   -0.3782   -1.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6050   -1.0981   -0.0941 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517   -1.7571    0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -0.7633    1.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2767    0.6199    0.7135 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8888    0.9331    1.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0005   -0.2677    0.8952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3611    0.2675    0.5097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7579    1.0605    1.6181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991   -0.8670    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171   -2.1816    0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9578   -3.1918    0.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1682   -2.8573   -0.0503 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5178   -1.5714   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7886   -1.2859   -0.7755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1310    0.0309   -1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2239    1.0520   -0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5776    2.3643   -1.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8271    2.7664   -1.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9679    0.7214   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5858   -0.5754   -0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4468    1.9015   -0.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5199    0.7058   -1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5977   -0.7133   -1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0656    2.5911   -0.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5463   -1.1599   -1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2944    0.0963   -1.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3456   -2.2931   -0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501   -2.5304    1.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7040   -0.9827    1.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2781   -0.7628    2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0316    1.3464    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9914    1.0442    2.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4729    1.8654    0.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8987   -0.8593    1.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823    0.8976   -0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3320    0.5583    2.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376   -2.4331    0.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545   -4.2026    0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4640   -2.1136   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1250    0.2423   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2031    2.0693   -2.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5152    2.7964   -0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7504    3.8124   -1.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303    1.4883   -0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  2  0
  9  3  1  0
 25 14  1  0
 11  6  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  6
 10 37  1  0
 10 38  1  0
 11 39  1  1
 12 40  1  6
 13 41  1  0
 15 42  1  0
 16 43  1  0
 19 44  1  0
 20 45  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.422  -2.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.084  -1.641   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.429  -3.945   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.748  -1.635   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.077  -0.103   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.249  -2.414   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.748  -4.718   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.097  -4.718   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -4.087  -2.407   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.261   0.663   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.410   0.676   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.242  -3.958   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.087  -3.945   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.419  -1.635   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       2.838   1.622   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.457   1.802   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.419  -0.097   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.838   2.980   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.486   0.740   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.008   2.723   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.015   3.810   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.720   1.957   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.435   5.239   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.096   4.911   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.381   6.455   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       1.860  -0.753   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.669   3.495   0.000  0.00  0.00           H+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13                                                       
CONECT    8    3   12                                                       
CONECT    9    4   14   13                                                  
CONECT   10    5   15   16   26                                             
CONECT   11    5                                                            
CONECT   12    6    8                                                       
CONECT   13    7    9                                                       
CONECT   14    9   17                                                       
CONECT   15   10   18   19                                                  
CONECT   16   10   20                                                       
CONECT   17   14                                                            
CONECT   18   15   21                                                       
CONECT   19   15   22                                                       
CONECT   20   16   21   22   27                                             
CONECT   21   18   23   24   20                                             
CONECT   22   19   20                                                       
CONECT   23   21   25                                                       
CONECT   24   21                                                            
CONECT   25   23                                                            
CONECT   26   10                                                            
CONECT   27   20                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0001091
HETATM    1  C1  UNL     1       5.538   0.964  -1.117  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.483   0.192  -1.331  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.164   0.599  -0.796  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.781   1.860  -1.216  1.00  0.00           O  
HETATM    5  C4  UNL     1       2.111  -0.378  -1.240  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.605  -1.098  -0.094  1.00  0.00           N  
HETATM    7  C5  UNL     1       2.752  -1.757   0.526  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.632  -0.763   1.251  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.277   0.620   0.713  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.889   0.933   1.248  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.000  -0.268   0.895  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.361   0.268   0.510  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.758   1.060   1.618  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.299  -0.867   0.330  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.017  -2.182   0.581  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.958  -3.192   0.391  1.00  0.00           C  
HETATM   17  N2  UNL     1      -3.168  -2.857  -0.050  1.00  0.00           N  
HETATM   18  C14 UNL     1      -3.518  -1.571  -0.320  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.789  -1.286  -0.775  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.131   0.031  -1.047  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.224   1.052  -0.869  1.00  0.00           C  
HETATM   22  O3  UNL     1      -4.578   2.364  -1.143  1.00  0.00           O  
HETATM   23  C18 UNL     1      -5.827   2.766  -1.605  1.00  0.00           C  
HETATM   24  C19 UNL     1      -2.968   0.721  -0.413  1.00  0.00           C  
HETATM   25  C20 UNL     1      -2.586  -0.575  -0.131  1.00  0.00           C  
HETATM   26  H1  UNL     1       5.447   1.901  -0.547  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.520   0.706  -1.488  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.598  -0.713  -1.886  1.00  0.00           H  
HETATM   29  H4  UNL     1       3.066   2.591  -0.634  1.00  0.00           H  
HETATM   30  H5  UNL     1       2.546  -1.160  -1.926  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.294   0.096  -1.825  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.346  -2.293  -0.240  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.350  -2.530   1.217  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.704  -0.983   1.159  1.00  0.00           H  
HETATM   35  H10 UNL     1       3.278  -0.763   2.318  1.00  0.00           H  
HETATM   36  H11 UNL     1       4.032   1.346   1.018  1.00  0.00           H  
HETATM   37  H12 UNL     1       1.991   1.044   2.349  1.00  0.00           H  
HETATM   38  H13 UNL     1       1.473   1.865   0.820  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.899  -0.859   1.833  1.00  0.00           H  
HETATM   40  H15 UNL     1      -0.282   0.898  -0.399  1.00  0.00           H  
HETATM   41  H16 UNL     1      -1.332   0.558   2.221  1.00  0.00           H  
HETATM   42  H17 UNL     1      -0.038  -2.433   0.939  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.655  -4.203   0.613  1.00  0.00           H  
HETATM   44  H19 UNL     1      -5.464  -2.114  -0.900  1.00  0.00           H  
HETATM   45  H20 UNL     1      -6.125   0.242  -1.401  1.00  0.00           H  
HETATM   46  H21 UNL     1      -6.203   2.069  -2.382  1.00  0.00           H  
HETATM   47  H22 UNL     1      -6.515   2.796  -0.718  1.00  0.00           H  
HETATM   48  H23 UNL     1      -5.750   3.812  -1.967  1.00  0.00           H  
HETATM   49  H24 UNL     1      -2.230   1.488  -0.261  1.00  0.00           H  
CONECT    1    2    2   26   27
CONECT    2    3   28
CONECT    3    4    5    9
CONECT    4   29
CONECT    5    6   30   31
CONECT    6    7   11
CONECT    7    8   32   33
CONECT    8    9   34   35
CONECT    9   10   36
CONECT   10   11   37   38
CONECT   11   12   39
CONECT   12   13   14   40
CONECT   13   41
CONECT   14   15   15   25
CONECT   15   16   42
CONECT   16   17   17   43
CONECT   17   18
CONECT   18   19   19   25
CONECT   19   20   44
CONECT   20   21   21   45
CONECT   21   22   24
CONECT   22   23
CONECT   23   46   47   48
CONECT   24   25   25   49
END

HMDB0001091
     RDKit          3D
3-Hydroxyquinine
 49 52  0  0  0  0  0  0  0  0999 V2000
    5.5381    0.9636   -1.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4831    0.1916   -1.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1641    0.5993   -0.7964 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7809    1.8596   -1.2155 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109   -0.3782   -1.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6050   -1.0981   -0.0941 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7517   -1.7571    0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -0.7633    1.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2767    0.6199    0.7135 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8888    0.9331    1.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0005   -0.2677    0.8952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3611    0.2675    0.5097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7579    1.0605    1.6181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991   -0.8670    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0171   -2.1816    0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9578   -3.1918    0.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1682   -2.8573   -0.0503 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5178   -1.5714   -0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7886   -1.2859   -0.7755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1310    0.0309   -1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2239    1.0520   -0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5776    2.3643   -1.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8271    2.7664   -1.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9679    0.7214   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5858   -0.5754   -0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4468    1.9015   -0.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5199    0.7058   -1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5977   -0.7133   -1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0656    2.5911   -0.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5463   -1.1599   -1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2944    0.0963   -1.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3456   -2.2931   -0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501   -2.5304    1.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7040   -0.9827    1.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2781   -0.7628    2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0316    1.3464    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9914    1.0442    2.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4729    1.8654    0.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8987   -0.8593    1.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823    0.8976   -0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3320    0.5583    2.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376   -2.4331    0.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545   -4.2026    0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4640   -2.1136   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1250    0.2423   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2031    2.0693   -2.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5152    2.7964   -0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7504    3.8124   -1.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303    1.4883   -0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  2  0
  9  3  1  0
 25 14  1  0
 11  6  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  6
 10 37  1  0
 10 38  1  0
 11 39  1  1
 12 40  1  6
 13 41  1  0
 15 42  1  0
 16 43  1  0
 19 44  1  0
 20 45  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxyquinidine	HMDB, MeSH
6'-Methoxycinchonan-3,9-diol	HMDB
3-Hydroxyquinidine, (3alpha,9S)-isomer	MeSH, HMDB
3-Hydroxyquinidine, (8alpha,9R)-isomer	MeSH, HMDB
3-Hydroxyquinine	MeSH

Chemical Formula

C₂₀H₂₄N₂O₃

Average Molecular Weight

340.4162

Monoisotopic Molecular Weight

340.178692644

IUPAC Name

(3S,4R,6S)-3-ethenyl-6-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol

Traditional Name

3-hydroxyquinidine

CAS Registry Number

53467-23-5

SMILES

[H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12

InChI Identifier

InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18+,19-,20-/m1/s1

InChI Key

BSRUJCFCZKMFMB-ZNYHDOEXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cinchona alkaloids

Sub Class

Not Available

Direct Parent

Cinchona alkaloids

Alternative Parents

Substituents

Cinchonan-skeleton
4-quinolinemethanol
Quinoline
Anisole
Quinuclidine
Alkyl aryl ether
Aralkylamine
Piperidine
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary alcohol
1,2-aminoalcohol
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Ether
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic alcohol
Alcohol
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Circulatory system disorder

Blood and lymphatic system disorder

Erythrocytic disorder

Malaria (HMDB: HMDB0001091)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12185554)

Excreta

Biofluid or Excreta

Feces (PMID: 29808030)

Source

Endogenous

Endogenous (HMDB: HMDB0001091)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.14 g/L	ALOGPS
logP	2.24	ALOGPS
logP	1.67	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	13.55	ChemAxon
pKa (Strongest Basic)	8.63	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.91 m³·mol⁻¹	ChemAxon
Polarizability	36.89 Å³	ChemAxon
Number of Rings	4	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]+	182.587	31661259
DarkChem	[M-H]-	176.457	31661259
AllCCS	[M+H]+	184.065	32859911
AllCCS	[M-H]-	188.252	32859911
DeepCCS	[M-2H]-	214.909	30932474
DeepCCS	[M+Na]+	190.158	30932474
AllCCS	[M+H]+	184.1	32859911
AllCCS	[M+H-H2O]+	180.9	32859911
AllCCS	[M+NH4]+	186.9	32859911
AllCCS	[M+Na]+	187.8	32859911
AllCCS	[M-H]-	188.3	32859911
AllCCS	[M+Na-2H]-	188.4	32859911
AllCCS	[M+HCOO]-	188.6	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.	2.49 minutes	32390414
Predicted by Siyang on May 30, 2022	9.45 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.73 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	258.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	637.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	219.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	123.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	291.8 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	275.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	891.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	603.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	49.5 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	516.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	169.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	231.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	681.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	635.0 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	151.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyquinine	[H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12	3504.6	Standard polar	33892256
3-Hydroxyquinine	[H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12	2834.8	Standard non polar	33892256
3-Hydroxyquinine	[H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12	3068.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxyquinine,1TMS,isomer #1	C=C[C@@]1(O[Si](C)(C)C)CN2CC[C@@H]1C[C@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C12	2746.2	Semi standard non polar	33892256
3-Hydroxyquinine,1TMS,isomer #2	C=C[C@@]1(O)CN2CC[C@@H]1C[C@H]2[C@H](O[Si](C)(C)C)C1=CC=NC2=CC=C(OC)C=C12	2773.5	Semi standard non polar	33892256
3-Hydroxyquinine,2TMS,isomer #1	C=C[C@@]1(O[Si](C)(C)C)CN2CC[C@@H]1C[C@H]2[C@H](O[Si](C)(C)C)C1=CC=NC2=CC=C(OC)C=C12	2775.4	Semi standard non polar	33892256
3-Hydroxyquinine,1TBDMS,isomer #1	C=C[C@@]1(O[Si](C)(C)C(C)(C)C)CN2CC[C@@H]1C[C@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C12	2999.1	Semi standard non polar	33892256
3-Hydroxyquinine,1TBDMS,isomer #2	C=C[C@@]1(O)CN2CC[C@@H]1C[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=NC2=CC=C(OC)C=C12	3024.9	Semi standard non polar	33892256
3-Hydroxyquinine,2TBDMS,isomer #1	C=C[C@@]1(O[Si](C)(C)C(C)(C)C)CN2CC[C@@H]1C[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=NC2=CC=C(OC)C=C12	3262.7	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 - 3-Hydroxyquinine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-2901000000-46662034299736c6d91a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyquinine GC-MS (2 TMS) - 70eV, Positive	splash10-03k9-4192400000-35f213d793369e0c6fa1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyquinine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxyquinine 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 - 3-Hydroxyquinine 10V, Positive-QTOF	splash10-00di-0009000000-757d948be08bc83ac896	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyquinine 20V, Positive-QTOF	splash10-0ab9-0409000000-0750a9802133c3ad7e0f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyquinine 40V, Positive-QTOF	splash10-053r-0911000000-f7b63c5080fbb178b639	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyquinine 10V, Negative-QTOF	splash10-000i-0009000000-c895e6c74087aa4b7c23	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyquinine 20V, Negative-QTOF	splash10-00dr-0119000000-8ff71092af9c3960da8e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyquinine 40V, Negative-QTOF	splash10-0uk9-0911000000-a23d26a2164f67414c08	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyquinine 10V, Negative-QTOF	splash10-000i-0009000000-6eb038badadf80b7dada	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyquinine 20V, Negative-QTOF	splash10-000b-0489000000-9bb3e6ff8d6f7f01ae22	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyquinine 40V, Negative-QTOF	splash10-08fr-0901000000-5fd6aa84f8079b3fc2d8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyquinine 10V, Positive-QTOF	splash10-0006-0009000000-3b43e0643b1819424eeb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyquinine 20V, Positive-QTOF	splash10-0006-0009000000-9364abb1565c929aab29	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxyquinine 40V, Positive-QTOF	splash10-00li-0961000000-7bb8ff583560fe8cdfb7	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.52 (2.35-4.40) uM	Adult (>18 years old)	Both	Malaria	12185554	details
Blood	Detected and Quantified	2.90 (1.76-6.16) uM	Adult (>18 years old)	Both	Malaria	12185554	details

Associated Disorders and Diseases

Disease References

Malaria
Pukrittayakamee S, Pitisuttithum P, Zhang H, Jantra A, Wanwimolruk S, White NJ: Effects of cigarette smoking on quinine pharmacokinetics in malaria. Eur J Clin Pharmacol. 2002 Aug;58(5):315-9. Epub 2002 Jun 20. [PubMed:12185554 ]

Associated OMIM IDs

248310 (Malaria)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022421

KNApSAcK ID

Not Available

Chemspider ID

138373

KEGG Compound ID

C07344

BioCyc ID

3-HYDROXYQUININE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

2234

PubChem Compound

441264

PDB ID

Not Available

ChEBI ID

17685

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Carroll, F. Ivy; Abraham, Philip; Gaetano, Kevan; Mascarella, S. Wayne; Wohl, Ronald A.; Lind, Joan; Petzoldt, Karl. (3S)-3-hydroxyquinidine, the major biotransformation product of quinidine. Synthesis and conformational studies. X-Ray molecular structure of (3S)-3-hydroxyquinidine methanesuiphonate. J. Chem. Soc., Perkin Trans. 1, 1991, 12, 3017-3026

Material Safety Data Sheet (MSDS)

Not Available

General References

Killeen AA, Bowers LD: Fetal supraventricular tachycardia treated with high-dose quinidine: toxicity associated with marked elevation of the metabolite, 3(S)-3-hydroxyquinidine. Obstet Gynecol. 1987 Sep;70(3 Pt 2):445-9. [PubMed:3627599 ]
Pukrittayakamee S, Wanwimolruk S, Stepniewska K, Jantra A, Huyakorn S, Looareesuwan S, White NJ: Quinine pharmacokinetic-pharmacodynamic relationships in uncomplicated falciparum malaria. Antimicrob Agents Chemother. 2003 Nov;47(11):3458-63. [PubMed:14576102 ]
Damkier P, Brosen K: Quinidine as a probe for CYP3A4 activity: intrasubject variability and lack of correlation with probe-based assays for CYP1A2, CYP2C9, CYP2C19, and CYP2D6. Clin Pharmacol Ther. 2000 Aug;68(2):199-209. [PubMed:10976551 ]
Ridtitid W, Wongnawa M, Mahatthanatrakul W, Raungsri N, Sunbhanich M: Ketoconazole increases plasma concentrations of antimalarial mefloquine in healthy human volunteers. J Clin Pharm Ther. 2005 Jun;30(3):285-90. [PubMed:15896247 ]
Christensen M, Andersson K, Dalen P, Mirghani RA, Muirhead GJ, Nordmark A, Tybring G, Wahlberg A, Yasar U, Bertilsson L: The Karolinska cocktail for phenotyping of five human cytochrome P450 enzymes. Clin Pharmacol Ther. 2003 Jun;73(6):517-28. [PubMed:12811361 ]
Mirghani RA, Hellgren U, Westerberg PA, Ericsson O, Bertilsson L, Gustafsson LL: The roles of cytochrome P450 3A4 and 1A2 in the 3-hydroxylation of quinine in vivo. Clin Pharmacol Ther. 1999 Nov;66(5):454-60. [PubMed:10579472 ]
Jansson A, Gustafsson LL, Mirghani RA: High-performance liquid chromatographic method for the determination of quinine and 3-hydroxyquinine in blood samples dried on filter paper. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Sep 25;795(1):151-6. [PubMed:12957180 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Reactions

Quinine + NADPH + Oxygen → 3-Hydroxyquinine + NADP + Water	details

Showing metabocard for 3-Hydroxyquinine (HMDB0001091)

MOL for HMDB0001091 (3-Hydroxyquinine)

3D MOL for HMDB0001091 (3-Hydroxyquinine)

3D SDF for HMDB0001091 (3-Hydroxyquinine)

3D-SDF for HMDB0001091 (3-Hydroxyquinine)

PDB for HMDB0001091 (3-Hydroxyquinine)

3D PDB for HMDB0001091 (3-Hydroxyquinine)

SMILES for HMDB0001091 (3-Hydroxyquinine)

INCHI for HMDB0001091 (3-Hydroxyquinine)

Structure for HMDB0001091 (3-Hydroxyquinine)

3D Structure for HMDB0001091 (3-Hydroxyquinine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions