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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:30 UTC

Update Date

2022-03-07 02:52:31 UTC

HMDB ID

HMDB0030390

Secondary Accession Numbers

HMDB30390

Metabolite Identification

Common Name

(+)-Quebrachidine

Description

(+)-Quebrachidine belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group. Based on a literature review a small amount of articles have been published on (+)-Quebrachidine.

Structure

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


  Mrv0541 05061305122D          

 26 31  0  0  0  0            999 V2000
    0.0074   -1.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1256    1.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1589   -0.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8991    0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1927    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0846    0.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6717   -0.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -0.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5619    1.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3449    0.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9370   -0.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5637    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5419   -0.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8572   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7335   -0.4876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8443    0.9635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5240   -0.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0494    1.2507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5105    1.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7397    0.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    0.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147   -0.9301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4535    0.3498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166    2.0586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7136    2.1257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7165    1.1021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
 11  3  2  0  0  0  0
 11 10  1  0  0  0  0
 12  6  2  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  2  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  6  0  0  0
 16  9  1  6  0  0  0
 17 15  1  0  0  0  0
 20  9  1  0  0  0  0
 20 12  1  0  0  0  0
 20 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 13  1  0  0  0  0
 21 16  1  0  0  0  0
 21 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 14  1  0  0  0  0
 22 17  1  0  0  0  0
 23 10  1  0  0  0  0
 23 15  1  0  0  0  0
 23 16  1  0  0  0  0
 18 24  1  1  0  0  0
 25 19  2  0  0  0  0
 26  2  1  0  0  0  0
 26 19  1  0  0  0  0
M  END

HMDB0030390
     RDKit          3D
(+)-Quebrachidine
 50 55  0  0  0  0  0  0  0  0999 V2000
   -4.5201    0.1226   -0.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8798   -1.0711    0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6087   -1.2745    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509   -2.4650    0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4536   -2.0735    0.5821 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727   -1.9944   -0.7610 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9450   -1.2638   -1.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -0.3209   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339    0.3292    0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    1.4404    0.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293    1.4246    2.1716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9882    2.4938    0.1827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6792    3.6106    0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4167   -0.7542    1.2352 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0496   -0.4619    1.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4614   -0.0902    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546    0.2644   -0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6121    1.3876    0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9844    1.4025   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6431    0.2682   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8924   -0.8691   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5197   -0.8877   -0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614   -1.9287   -0.6549 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3382   -1.2590   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4335    0.9014   -0.3313 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6771    2.1918    0.0690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3530    0.2547   -1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6370   -0.0273   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3295    1.0563    0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4255   -1.8052    0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9687   -3.3190   -0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1751   -2.6848    1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1399   -3.0213   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6516   -1.9764   -2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4494   -0.7165   -2.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255    0.4072   -1.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7525    3.6118    0.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1784    4.5127    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769    3.6782    1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0063   -0.8149    2.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6090   -1.3178    1.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    0.4480    2.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843    2.2871    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5731    2.2912    0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7299    0.2801   -0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4435   -1.7573   -1.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486   -2.9360   -0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103   -0.8042   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3256    0.9173   -1.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130    2.3132    1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 16 25  1  0
 25 26  1  0
  8  3  1  0
 25  9  1  0
 14  5  1  0
 24 16  1  0
 24  6  1  0
 22 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  6 33  1  6
  7 34  1  0
  7 35  1  0
  8 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  1
 15 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  6
 26 50  1  0
M  END


  Mrv0541 05061305122D          

 26 31  0  0  0  0            999 V2000
    0.0074   -1.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1256    1.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1589   -0.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8991    0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1927    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0846    0.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6717   -0.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -0.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5619    1.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3449    0.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9370   -0.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5637    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5419   -0.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8572   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7335   -0.4876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8443    0.9635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5240   -0.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0494    1.2507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5105    1.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7397    0.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    0.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147   -0.9301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4535    0.3498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166    2.0586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7136    2.1257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7165    1.1021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
 11  3  2  0  0  0  0
 11 10  1  0  0  0  0
 12  6  2  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  2  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  6  0  0  0
 16  9  1  6  0  0  0
 17 15  1  0  0  0  0
 20  9  1  0  0  0  0
 20 12  1  0  0  0  0
 20 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 13  1  0  0  0  0
 21 16  1  0  0  0  0
 21 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 14  1  0  0  0  0
 22 17  1  0  0  0  0
 23 10  1  0  0  0  0
 23 15  1  0  0  0  0
 23 16  1  0  0  0  0
 18 24  1  1  0  0  0
 25 19  2  0  0  0  0
 26  2  1  0  0  0  0
 26 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030390

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C12[C@@H]3CC4(C(NC5=CC=CC=C45)[C@@H]4CC1\C(CN34)=C/C)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O3/c1-3-11-10-23-15-8-13(11)21(19(25)26-2)16(23)9-20(18(21)24)12-6-4-5-7-14(12)22-17(15)20/h3-7,13,15-18,22,24H,8-10H2,1-2H3/b11-3-/t13?,15-,16-,17?,18-,20?,21?/m0/s1

> <INCHI_KEY>
RLUORQGMBKDXPO-CFAUMIGUSA-N

> <FORMULA>
C21H24N2O3

> <MOLECULAR_WEIGHT>
352.4269

> <EXACT_MASS>
352.178692644

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.08096031986682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (10S,13E,16S,18S)-13-ethylidene-18-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
1.1964292169999995

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.924427501442846

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.848527472138645

> <JCHEM_PKA_STRONGEST_BASIC>
6.976584822316992

> <JCHEM_POLAR_SURFACE_AREA>
61.8

> <JCHEM_REFRACTIVITY>
98.84809999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (10S,13E,16S,18S)-13-ethylidene-18-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030390
     RDKit          3D
(+)-Quebrachidine
 50 55  0  0  0  0  0  0  0  0999 V2000
   -4.5201    0.1226   -0.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8798   -1.0711    0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6087   -1.2745    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509   -2.4650    0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4536   -2.0735    0.5821 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727   -1.9944   -0.7610 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9450   -1.2638   -1.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -0.3209   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339    0.3292    0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    1.4404    0.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293    1.4246    2.1716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9882    2.4938    0.1827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6792    3.6106    0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4167   -0.7542    1.2352 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0496   -0.4619    1.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4614   -0.0902    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546    0.2644   -0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6121    1.3876    0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9844    1.4025   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6431    0.2682   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8924   -0.8691   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5197   -0.8877   -0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614   -1.9287   -0.6549 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3382   -1.2590   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4335    0.9014   -0.3313 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6771    2.1918    0.0690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3530    0.2547   -1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6370   -0.0273   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3295    1.0563    0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4255   -1.8052    0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9687   -3.3190   -0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1751   -2.6848    1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1399   -3.0213   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6516   -1.9764   -2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4494   -0.7165   -2.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255    0.4072   -1.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7525    3.6118    0.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1784    4.5127    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769    3.6782    1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0063   -0.8149    2.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6090   -1.3178    1.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    0.4480    2.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843    2.2871    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5731    2.2912    0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7299    0.2801   -0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4435   -1.7573   -1.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486   -2.9360   -0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103   -0.8042   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3256    0.9173   -1.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130    2.3132    1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 16 25  1  0
 25 26  1  0
  8  3  1  0
 25  9  1  0
 14  5  1  0
 24 16  1  0
 24  6  1  0
 22 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  6 33  1  6
  7 34  1  0
  7 35  1  0
  8 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  1
 15 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  6
 26 50  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.014  -2.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.234   3.132   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.297  -0.827   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.012   1.618   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.560   0.179   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.491   1.863   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.587  -1.015   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.955  -1.776   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.649   1.995   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.510   0.911   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.749  -0.315   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.519   0.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.878  -0.711   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.067  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.103  -0.910   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.309   1.799   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.578  -0.894   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.692   2.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.820   2.475   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.981   0.592   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.923   1.401   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       7.867  -1.736   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       4.580   0.653   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       6.004   3.843   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.199   3.968   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.337   2.057   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   26                                                            
CONECT    3    1   11                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   14                                                       
CONECT    8   13   15                                                       
CONECT    9   16   20                                                       
CONECT   10   11   23                                                       
CONECT   11    3   10   13                                                  
CONECT   12    6   14   20                                                  
CONECT   13    8   11   21                                                  
CONECT   14    7   12   22                                                  
CONECT   15    8   17   23                                                  
CONECT   16    9   21   23                                                  
CONECT   17   15   20   22                                                  
CONECT   18   20   21   24                                                  
CONECT   19   21   25   26                                                  
CONECT   20    9   12   17   18                                             
CONECT   21   13   16   18   19                                             
CONECT   22   14   17                                                       
CONECT   23   10   15   16                                                  
CONECT   24   18                                                            
CONECT   25   19                                                            
CONECT   26    2   19                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

COMPND    HMDB0030390
HETATM    1  C1  UNL     1      -4.520   0.123  -0.328  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.880  -1.071   0.241  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.609  -1.274   0.050  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.851  -2.465   0.588  1.00  0.00           C  
HETATM    5  N1  UNL     1      -0.454  -2.073   0.582  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.073  -1.994  -0.761  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.945  -1.264  -1.657  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.746  -0.321  -0.745  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.834   0.329   0.286  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.539   1.440   0.936  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.729   1.425   2.172  1.00  0.00           O  
HETATM   12  O2  UNL     1      -1.988   2.494   0.183  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.679   3.611   0.724  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.417  -0.754   1.235  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.050  -0.462   1.467  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.461  -0.090   0.058  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.855   0.264  -0.066  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.612   1.388   0.137  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.984   1.402  -0.067  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.643   0.268  -0.487  1.00  0.00           C  
HETATM   21  C18 UNL     1       4.892  -0.869  -0.695  1.00  0.00           C  
HETATM   22  C19 UNL     1       3.520  -0.888  -0.493  1.00  0.00           C  
HETATM   23  N2  UNL     1       2.561  -1.929  -0.655  1.00  0.00           N  
HETATM   24  C20 UNL     1       1.338  -1.259  -0.899  1.00  0.00           C  
HETATM   25  C21 UNL     1       0.434   0.901  -0.331  1.00  0.00           C  
HETATM   26  O3  UNL     1       0.677   2.192   0.069  1.00  0.00           O  
HETATM   27  H1  UNL     1      -4.353   0.255  -1.416  1.00  0.00           H  
HETATM   28  H2  UNL     1      -5.637  -0.027  -0.236  1.00  0.00           H  
HETATM   29  H3  UNL     1      -4.330   1.056   0.254  1.00  0.00           H  
HETATM   30  H4  UNL     1      -4.425  -1.805   0.824  1.00  0.00           H  
HETATM   31  H5  UNL     1      -1.969  -3.319  -0.120  1.00  0.00           H  
HETATM   32  H6  UNL     1      -2.175  -2.685   1.607  1.00  0.00           H  
HETATM   33  H7  UNL     1       0.140  -3.021  -1.151  1.00  0.00           H  
HETATM   34  H8  UNL     1      -1.652  -1.976  -2.117  1.00  0.00           H  
HETATM   35  H9  UNL     1      -0.449  -0.717  -2.461  1.00  0.00           H  
HETATM   36  H10 UNL     1      -2.326   0.407  -1.306  1.00  0.00           H  
HETATM   37  H11 UNL     1      -3.752   3.612   0.443  1.00  0.00           H  
HETATM   38  H12 UNL     1      -2.178   4.513   0.273  1.00  0.00           H  
HETATM   39  H13 UNL     1      -2.577   3.678   1.822  1.00  0.00           H  
HETATM   40  H14 UNL     1      -1.006  -0.815   2.148  1.00  0.00           H  
HETATM   41  H15 UNL     1       1.609  -1.318   1.862  1.00  0.00           H  
HETATM   42  H16 UNL     1       1.142   0.448   2.079  1.00  0.00           H  
HETATM   43  H17 UNL     1       3.084   2.287   0.470  1.00  0.00           H  
HETATM   44  H18 UNL     1       5.573   2.291   0.095  1.00  0.00           H  
HETATM   45  H19 UNL     1       6.730   0.280  -0.647  1.00  0.00           H  
HETATM   46  H20 UNL     1       5.444  -1.757  -1.029  1.00  0.00           H  
HETATM   47  H21 UNL     1       2.749  -2.936  -0.601  1.00  0.00           H  
HETATM   48  H22 UNL     1       1.410  -0.804  -1.921  1.00  0.00           H  
HETATM   49  H23 UNL     1       0.326   0.917  -1.452  1.00  0.00           H  
HETATM   50  H24 UNL     1       0.713   2.313   1.036  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    3   30
CONECT    3    4    8
CONECT    4    5   31   32
CONECT    5    6   14
CONECT    6    7   24   33
CONECT    7    8   34   35
CONECT    8    9   36
CONECT    9   10   14   25
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   37   38   39
CONECT   14   15   40
CONECT   15   16   41   42
CONECT   16   17   24   25
CONECT   17   18   18   22
CONECT   18   19   43
CONECT   19   20   20   44
CONECT   20   21   45
CONECT   21   22   22   46
CONECT   22   23
CONECT   23   24   47
CONECT   24   48
CONECT   25   26   49
CONECT   26   50
END

HMDB0030390
     RDKit          3D
(+)-Quebrachidine
 50 55  0  0  0  0  0  0  0  0999 V2000
   -4.5201    0.1226   -0.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8798   -1.0711    0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6087   -1.2745    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509   -2.4650    0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4536   -2.0735    0.5821 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0727   -1.9944   -0.7610 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9450   -1.2638   -1.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -0.3209   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339    0.3292    0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    1.4404    0.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7293    1.4246    2.1716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9882    2.4938    0.1827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6792    3.6106    0.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4167   -0.7542    1.2352 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0496   -0.4619    1.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4614   -0.0902    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546    0.2644   -0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6121    1.3876    0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9844    1.4025   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6431    0.2682   -0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8924   -0.8691   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5197   -0.8877   -0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614   -1.9287   -0.6549 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3382   -1.2590   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4335    0.9014   -0.3313 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6771    2.1918    0.0690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3530    0.2547   -1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6370   -0.0273   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3295    1.0563    0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4255   -1.8052    0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9687   -3.3190   -0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1751   -2.6848    1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1399   -3.0213   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6516   -1.9764   -2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4494   -0.7165   -2.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255    0.4072   -1.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7525    3.6118    0.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1784    4.5127    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769    3.6782    1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0063   -0.8149    2.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6090   -1.3178    1.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    0.4480    2.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843    2.2871    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5731    2.2912    0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7299    0.2801   -0.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4435   -1.7573   -1.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486   -2.9360   -0.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103   -0.8042   -1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3256    0.9173   -1.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130    2.3132    1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 16 25  1  0
 25 26  1  0
  8  3  1  0
 25  9  1  0
 14  5  1  0
 24 16  1  0
 24  6  1  0
 22 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  6 33  1  6
  7 34  1  0
  7 35  1  0
  8 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  1
 15 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  6
 26 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Cyanomethylene-1-glucosyloxy-3-hydroxy-4,5-dimethoxycyclohexane	HMDB
[6-(b-D-Glucopyranosyloxy)-2-hydroxy-3,4-dimethoxycyclohexylidene]acetonitrile, 9ci	HMDB
2-(Cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl-beta-glucoside	HMDB
Methyl (10S,13E,16S,18S)-13-ethylidene-18-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylic acid	HMDB

Chemical Formula

C₂₁H₂₄N₂O₃

Average Molecular Weight

352.4269

Monoisotopic Molecular Weight

352.178692644

IUPAC Name

methyl (10S,13E,16S,18S)-13-ethylidene-18-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

Traditional Name

methyl (10S,13E,16S,18S)-13-ethylidene-18-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-triene-17-carboxylate

CAS Registry Number

21641-60-1

SMILES

COC(=O)C12[C@@H]3CC4(C(NC5=CC=CC=C45)[C@@H]4CC1\C(CN34)=C/C)[C@@H]2O

InChI Identifier

InChI=1S/C21H24N2O3/c1-3-11-10-23-15-8-13(11)21(19(25)26-2)16(23)9-20(18(21)24)12-6-4-5-7-14(12)22-17(15)20/h3-7,13,15-18,22,24H,8-10H2,1-2H3/b11-3-/t13?,15-,16-,17?,18-,20?,21?/m0/s1

InChI Key

RLUORQGMBKDXPO-CFAUMIGUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Corynanthean-type alkaloids

Sub Class

Not Available

Direct Parent

Corynanthean-type alkaloids

Alternative Parents

Substituents

Corynanthean skeleton
Beta-carboline
Pyridoindole
Delta amino acid or derivatives
Quinolizidine
Indole or derivatives
Dihydroindole
Piperidinecarboxylic acid
Quinuclidine
Azepane
Beta-hydroxy acid
Aralkylamine
Secondary aliphatic/aromatic amine
Hydroxy acid
Benzenoid
Piperidine
Cyclic alcohol
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Secondary amine
Alcohol
Hydrocarbon derivative
Organic oxide
Amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030390)
Cytoplasm (HMDB: HMDB0030390)

Source

Endogenous

Endogenous (HMDB: HMDB0030390)

Exogenous

Food

Food (HMDB: HMDB0030390)

Exogenous (HMDB: HMDB0030390)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	263 - 264 °C	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	3.17 g/L	ALOGPS
logP	2.38	ALOGPS
logP	1.2	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	6.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.8 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.85 m³·mol⁻¹	ChemAxon
Polarizability	38.08 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	179.027	31661259
DarkChem	[M-H]-	175.8	31661259
DeepCCS	[M-2H]-	222.252	30932474
DeepCCS	[M+Na]+	197.619	30932474
AllCCS	[M+H]+	186.9	32859911
AllCCS	[M+H-H2O]+	184.1	32859911
AllCCS	[M+NH4]+	189.6	32859911
AllCCS	[M+Na]+	190.3	32859911
AllCCS	[M-H]-	192.8	32859911
AllCCS	[M+Na-2H]-	192.5	32859911
AllCCS	[M+HCOO]-	192.4	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.	4.51 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1307 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.52 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1391.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	190.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	134.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	54.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	246.3 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	317.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	344.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	731.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	338.0 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	863.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	218.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	297.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	286.5 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	62.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-Quebrachidine	COC(=O)C12[C@@H]3CC4(C(NC5=CC=CC=C45)[C@@H]4CC1\C(CN34)=C/C)[C@@H]2O	4254.6	Standard polar	33892256
(+)-Quebrachidine	COC(=O)C12[C@@H]3CC4(C(NC5=CC=CC=C45)[C@@H]4CC1\C(CN34)=C/C)[C@@H]2O	2798.5	Standard non polar	33892256
(+)-Quebrachidine	COC(=O)C12[C@@H]3CC4(C(NC5=CC=CC=C45)[C@@H]4CC1\C(CN34)=C/C)[C@@H]2O	2830.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+)-Quebrachidine,1TMS,isomer #1	C/C=C1/CN2[C@H]3CC1C1(C(=O)OC)[C@@H]2CC2(C4=CC=CC=C4NC32)[C@@H]1O[Si](C)(C)C	2818.5	Semi standard non polar	33892256
(+)-Quebrachidine,1TMS,isomer #2	C/C=C1/CN2[C@H]3CC1C1(C(=O)OC)[C@@H]2CC2(C4=CC=CC=C4N([Si](C)(C)C)C32)[C@@H]1O	2736.0	Semi standard non polar	33892256
(+)-Quebrachidine,2TMS,isomer #1	C/C=C1/CN2[C@H]3CC1C1(C(=O)OC)[C@@H]2CC2(C4=CC=CC=C4N([Si](C)(C)C)C32)[C@@H]1O[Si](C)(C)C	2757.7	Semi standard non polar	33892256
(+)-Quebrachidine,2TMS,isomer #1	C/C=C1/CN2[C@H]3CC1C1(C(=O)OC)[C@@H]2CC2(C4=CC=CC=C4N([Si](C)(C)C)C32)[C@@H]1O[Si](C)(C)C	2858.7	Standard non polar	33892256
(+)-Quebrachidine,1TBDMS,isomer #1	C/C=C1/CN2[C@H]3CC1C1(C(=O)OC)[C@@H]2CC2(C4=CC=CC=C4NC32)[C@@H]1O[Si](C)(C)C(C)(C)C	3016.9	Semi standard non polar	33892256
(+)-Quebrachidine,1TBDMS,isomer #2	C/C=C1/CN2[C@H]3CC1C1(C(=O)OC)[C@@H]2CC2(C4=CC=CC=C4N([Si](C)(C)C(C)(C)C)C32)[C@@H]1O	2934.4	Semi standard non polar	33892256
(+)-Quebrachidine,2TBDMS,isomer #1	C/C=C1/CN2[C@H]3CC1C1(C(=O)OC)[C@@H]2CC2(C4=CC=CC=C4N([Si](C)(C)C(C)(C)C)C32)[C@@H]1O[Si](C)(C)C(C)(C)C	3121.9	Semi standard non polar	33892256
(+)-Quebrachidine,2TBDMS,isomer #1	C/C=C1/CN2[C@H]3CC1C1(C(=O)OC)[C@@H]2CC2(C4=CC=CC=C4N([Si](C)(C)C(C)(C)C)C32)[C@@H]1O[Si](C)(C)C(C)(C)C	3370.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Quebrachidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0076-3049000000-1512485f53dac99bd342	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Quebrachidine GC-MS (1 TMS) - 70eV, Positive	splash10-05g3-9004200000-c80d0efaafffc8a45e86	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Quebrachidine 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 - (+)-Quebrachidine 10V, Positive-QTOF	splash10-0udr-0009000000-861a7ed16f2918f700dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Quebrachidine 20V, Positive-QTOF	splash10-0ug0-0029000000-0985fd508474fa418573	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Quebrachidine 40V, Positive-QTOF	splash10-004i-2096000000-e2bc058d27a511d00e0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Quebrachidine 10V, Negative-QTOF	splash10-0udi-0009000000-00bda9e8ec0b8b34a52a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Quebrachidine 20V, Negative-QTOF	splash10-0udi-0019000000-fb75b362b0dd374df4c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Quebrachidine 40V, Negative-QTOF	splash10-00ko-0093000000-62d75063c7fd5ac92e6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Quebrachidine 10V, Positive-QTOF	splash10-0udi-0019000000-40c487ceb6e346a1aed9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Quebrachidine 20V, Positive-QTOF	splash10-0udi-0029000000-db598bf64510018ca56e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Quebrachidine 40V, Positive-QTOF	splash10-0udl-0069000000-8a9e1f50c6e35e081fcf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Quebrachidine 10V, Negative-QTOF	splash10-0udi-0049000000-63bd1a6a9039fd137926	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Quebrachidine 20V, Negative-QTOF	splash10-0006-0090000000-a47e1d5b96b417632a5c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Quebrachidine 40V, Negative-QTOF	splash10-0006-0090000000-4e71703a18aaccacc836	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002243

KNApSAcK ID

Not Available

Chemspider ID

4733931

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Simmondsin

METLIN ID

Not Available

PubChem Compound

6445097

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (+)-Quebrachidine (HMDB0030390)

MOL for HMDB0030390 ((+)-Quebrachidine)

3D MOL for HMDB0030390 ((+)-Quebrachidine)

3D SDF for HMDB0030390 ((+)-Quebrachidine)

3D-SDF for HMDB0030390 ((+)-Quebrachidine)

PDB for HMDB0030390 ((+)-Quebrachidine)

3D PDB for HMDB0030390 ((+)-Quebrachidine)

SMILES for HMDB0030390 ((+)-Quebrachidine)

INCHI for HMDB0030390 ((+)-Quebrachidine)

Structure for HMDB0030390 ((+)-Quebrachidine)

3D Structure for HMDB0030390 ((+)-Quebrachidine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra