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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:53:50 UTC

Update Date

2022-03-07 02:56:34 UTC

HMDB ID

HMDB0040369

Secondary Accession Numbers

HMDB40369

Metabolite Identification

Common Name

Huajiaosimuline

Description

Huajiaosimuline belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. Huajiaosimuline has been detected, but not quantified in, fruits and herbs and spices. This could make huajiaosimuline a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Huajiaosimuline.

Structure

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

HMDB0040369
     RDKit          3D
Huajiaosimuline
 47 49  0  0  0  0  0  0  0  0999 V2000
    5.8533   -0.6549    0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9598   -0.1736   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    1.2619   -0.1569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710   -1.0670   -0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7112   -1.9885    0.2357 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6761   -0.8802   -1.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4956   -0.1360   -1.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736   -0.6388    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3310   -0.7861    1.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1437   -1.9811   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207   -2.2222   -0.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1283   -1.1865   -0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099    0.0774    0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6525    1.0775    0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2318    2.3458    0.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1829    3.3281    0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5364    3.0894    0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9248    1.8108    0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9964    0.7842    0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4039   -0.4557   -0.2669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8131   -0.7478   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4746   -1.4141   -0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8268   -2.5990   -0.7391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3835    0.3222    0.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8786   -0.2492    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8152   -1.7495    0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4486   -0.2114    1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227   -0.1963   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9554    1.2819    0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4700    1.8698    0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0811    1.7319   -1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4342   -1.8470   -2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434   -0.2769   -2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7724   -0.0083   -1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8193    0.9387   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -1.8390    1.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966   -0.3874    2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2184   -0.1448    1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8528   -2.7735   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216   -3.2058   -0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1911    2.6057    0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8429    4.3140    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2546    3.8860    0.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9783    1.6191    0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1288   -0.1956   -1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4257   -0.4992    0.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9209   -1.8290   -0.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 13 24  1  0
 24  8  1  0
 22 12  1  0
 19 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
M  END


  Mrv0541 05061311472D          

 24 26  0  0  0  0            999 V2000
    1.6771    3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    4.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8364    0.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1451    2.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4273    2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3327    3.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8970    1.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6471    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663    3.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3650    2.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808    3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    3.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8024    2.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845    1.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481    3.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9899    2.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418    1.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953    3.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5542    1.0007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481    4.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2115    0.5120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7077    3.3265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 14  7  2  0  0  0  0
 15  9  1  0  0  0  0
 16  8  2  0  0  0  0
 16 14  1  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  2  0  0  0  0
 19 15  1  0  0  0  0
 20  3  1  0  0  0  0
 20 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21  4  1  0  0  0  0
 21 16  1  0  0  0  0
 21 19  1  0  0  0  0
 22 17  2  0  0  0  0
 23 19  2  0  0  0  0
 24 18  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040369

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C(=O)CCC1(C)OC2=C(C=C1)C(=O)N(C)C1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO3/c1-13(2)17(22)10-12-20(3)11-9-15-18(24-20)14-7-5-6-8-16(14)21(4)19(15)23/h5-9,11,13H,10,12H2,1-4H3

> <INCHI_KEY>
NYATVLNHGXEKDI-UHFFFAOYSA-N

> <FORMULA>
C20H23NO3

> <MOLECULAR_WEIGHT>
325.4015

> <EXACT_MASS>
325.167793607

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.07319694578644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dimethyl-2-(4-methyl-3-oxopentyl)-2H,5H,6H-pyrano[3,2-c]quinolin-5-one

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
2.898209611333333

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.548787648500014

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9438739733003442

> <JCHEM_POLAR_SURFACE_AREA>
46.61

> <JCHEM_REFRACTIVITY>
95.82759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dimethyl-2-(4-methyl-3-oxopentyl)pyrano[3,2-c]quinolin-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040369
     RDKit          3D
Huajiaosimuline
 47 49  0  0  0  0  0  0  0  0999 V2000
    5.8533   -0.6549    0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9598   -0.1736   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    1.2619   -0.1569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710   -1.0670   -0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7112   -1.9885    0.2357 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6761   -0.8802   -1.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4956   -0.1360   -1.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736   -0.6388    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3310   -0.7861    1.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1437   -1.9811   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207   -2.2222   -0.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1283   -1.1865   -0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099    0.0774    0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6525    1.0775    0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2318    2.3458    0.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1829    3.3281    0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5364    3.0894    0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9248    1.8108    0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9964    0.7842    0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4039   -0.4557   -0.2669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8131   -0.7478   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4746   -1.4141   -0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8268   -2.5990   -0.7391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3835    0.3222    0.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8786   -0.2492    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8152   -1.7495    0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4486   -0.2114    1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227   -0.1963   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9554    1.2819    0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4700    1.8698    0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0811    1.7319   -1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4342   -1.8470   -2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434   -0.2769   -2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7724   -0.0083   -1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8193    0.9387   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -1.8390    1.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966   -0.3874    2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2184   -0.1448    1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8528   -2.7735   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216   -3.2058   -0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1911    2.6057    0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8429    4.3140    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2546    3.8860    0.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9783    1.6191    0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1288   -0.1956   -1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4257   -0.4992    0.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9209   -1.8290   -0.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 13 24  1  0
 24  8  1  0
 22 12  1  0
 19 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  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       3.131   7.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.797   4.937   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.064   7.924   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.161   0.421   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.604   5.407   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.131   3.960   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.088   5.675   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.141   2.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.075   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.870   6.477   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.548   5.297   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.204   7.247   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.797   6.477   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.098   4.495   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.591   3.583   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.624   3.048   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.463   7.247   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.581   4.762   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.118   2.135   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.538   6.477   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -6.635   1.868   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       0.463   8.787   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.128   0.956   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.054   6.209   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5   14                                                       
CONECT    8    6   16                                                       
CONECT    9   11   15                                                       
CONECT   10   12   17                                                       
CONECT   11    9   20                                                       
CONECT   12   10   20                                                       
CONECT   13    1    2   17                                                  
CONECT   14    7   16   18                                                  
CONECT   15    9   18   19                                                  
CONECT   16    8   14   21                                                  
CONECT   17   10   13   22                                                  
CONECT   18   14   15   24                                                  
CONECT   19   15   21   23                                                  
CONECT   20    3   11   12   24                                             
CONECT   21    4   16   19                                                  
CONECT   22   17                                                            
CONECT   23   19                                                            
CONECT   24   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0040369
HETATM    1  C1  UNL     1       5.853  -0.655   0.634  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.960  -0.174  -0.485  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.564   1.262  -0.157  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.771  -1.067  -0.552  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.711  -1.988   0.236  1.00  0.00           O  
HETATM    6  C5  UNL     1       2.676  -0.880  -1.527  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.496  -0.136  -1.080  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.674  -0.639   0.046  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.331  -0.786   1.373  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.144  -1.981  -0.312  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.121  -2.222  -0.459  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.128  -1.187  -0.282  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.710   0.077   0.050  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.652   1.078   0.224  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.232   2.346   0.558  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.183   3.328   0.728  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.536   3.089   0.576  1.00  0.00           C  
HETATM   18  C17 UNL     1      -4.925   1.811   0.241  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.996   0.784   0.059  1.00  0.00           C  
HETATM   20  N1  UNL     1      -4.404  -0.456  -0.267  1.00  0.00           N  
HETATM   21  C19 UNL     1      -5.813  -0.748  -0.437  1.00  0.00           C  
HETATM   22  C20 UNL     1      -3.475  -1.414  -0.431  1.00  0.00           C  
HETATM   23  O2  UNL     1      -3.827  -2.599  -0.739  1.00  0.00           O  
HETATM   24  O3  UNL     1      -0.383   0.322   0.202  1.00  0.00           O  
HETATM   25  H1  UNL     1       6.879  -0.249   0.530  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.815  -1.750   0.765  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.449  -0.211   1.578  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.523  -0.196  -1.462  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.955   1.282   0.764  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.470   1.870   0.079  1.00  0.00           H  
HETATM   31  H7  UNL     1       4.081   1.732  -1.037  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.434  -1.847  -2.057  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.143  -0.277  -2.372  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.772  -0.008  -1.947  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.819   0.939  -0.897  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.461  -1.839   1.704  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.597  -0.387   2.149  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.218  -0.145   1.532  1.00  0.00           H  
HETATM   39  H15 UNL     1       0.853  -2.773  -0.452  1.00  0.00           H  
HETATM   40  H16 UNL     1      -1.522  -3.206  -0.722  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.191   2.606   0.694  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.843   4.314   0.990  1.00  0.00           H  
HETATM   43  H19 UNL     1      -5.255   3.886   0.718  1.00  0.00           H  
HETATM   44  H20 UNL     1      -5.978   1.619   0.121  1.00  0.00           H  
HETATM   45  H21 UNL     1      -6.129  -0.196  -1.357  1.00  0.00           H  
HETATM   46  H22 UNL     1      -6.426  -0.499   0.434  1.00  0.00           H  
HETATM   47  H23 UNL     1      -5.921  -1.829  -0.678  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   28
CONECT    3   29   30   31
CONECT    4    5    5    6
CONECT    6    7   32   33
CONECT    7    8   34   35
CONECT    8    9   10   24
CONECT    9   36   37   38
CONECT   10   11   11   39
CONECT   11   12   40
CONECT   12   13   13   22
CONECT   13   14   24
CONECT   14   15   15   19
CONECT   15   16   41
CONECT   16   17   17   42
CONECT   17   18   43
CONECT   18   19   19   44
CONECT   19   20
CONECT   20   21   22
CONECT   21   45   46   47
CONECT   22   23   23
END

HMDB0040369
     RDKit          3D
Huajiaosimuline
 47 49  0  0  0  0  0  0  0  0999 V2000
    5.8533   -0.6549    0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9598   -0.1736   -0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    1.2619   -0.1569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710   -1.0670   -0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7112   -1.9885    0.2357 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6761   -0.8802   -1.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4956   -0.1360   -1.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736   -0.6388    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3310   -0.7861    1.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1437   -1.9811   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207   -2.2222   -0.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1283   -1.1865   -0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099    0.0774    0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6525    1.0775    0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2318    2.3458    0.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1829    3.3281    0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5364    3.0894    0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9248    1.8108    0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9964    0.7842    0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4039   -0.4557   -0.2669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8131   -0.7478   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4746   -1.4141   -0.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8268   -2.5990   -0.7391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3835    0.3222    0.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8786   -0.2492    0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8152   -1.7495    0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4486   -0.2114    1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227   -0.1963   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9554    1.2819    0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4700    1.8698    0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0811    1.7319   -1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4342   -1.8470   -2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434   -0.2769   -2.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7724   -0.0083   -1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8193    0.9387   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -1.8390    1.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966   -0.3874    2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2184   -0.1448    1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8528   -2.7735   -0.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216   -3.2058   -0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1911    2.6057    0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8429    4.3140    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2546    3.8860    0.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9783    1.6191    0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1288   -0.1956   -1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4257   -0.4992    0.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9209   -1.8290   -0.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 13 24  1  0
 24  8  1  0
 22 12  1  0
 19 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₃NO₃

Average Molecular Weight

325.4015

Monoisotopic Molecular Weight

325.167793607

IUPAC Name

2,6-dimethyl-2-(4-methyl-3-oxopentyl)-2H,5H,6H-pyrano[3,2-c]quinolin-5-one

Traditional Name

2,6-dimethyl-2-(4-methyl-3-oxopentyl)pyrano[3,2-c]quinolin-5-one

CAS Registry Number

155416-21-0

SMILES

CC(C)C(=O)CCC1(C)OC2=C(C=C1)C(=O)N(C)C1=CC=CC=C21

InChI Identifier

InChI=1S/C20H23NO3/c1-13(2)17(22)10-12-20(3)11-9-15-18(24-20)14-7-5-6-8-16(14)21(4)19(15)23/h5-9,11,13H,10,12H2,1-4H3

InChI Key

NYATVLNHGXEKDI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Pyranoquinolines

Alternative Parents

Substituents

Pyranoquinoline
Dihydroquinolone
Dihydroquinoline
Pyranopyridine
Alkyl aryl ether
Pyridinone
Pyran
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous ester
Ketone
Lactam
Ether
Oxacycle
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0040369)

Cellular substructure

Membrane (HMDB: HMDB0040369)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040369)

Source

Exogenous

Food

Food (HMDB: HMDB0040369)

Fruit

Fruits (FooDB: FOOD00871)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0040369)

Not Available

Nutrient (HMDB: HMDB0040369)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	85.33 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.055 g/L	ALOGPS
logP	3.18	ALOGPS
logP	2.9	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.55	ChemAxon
pKa (Strongest Basic)	-0.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.61 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.83 m³·mol⁻¹	ChemAxon
Polarizability	36.07 Å³	ChemAxon
Number of Rings	3	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]+	177.288	31661259
DarkChem	[M-H]-	175.161	31661259
DeepCCS	[M-2H]-	216.461	30932474
DeepCCS	[M+Na]+	192.228	30932474
AllCCS	[M+H]+	178.8	32859911
AllCCS	[M+H-H2O]+	175.4	32859911
AllCCS	[M+NH4]+	181.9	32859911
AllCCS	[M+Na]+	182.8	32859911
AllCCS	[M-H]-	186.5	32859911
AllCCS	[M+Na-2H]-	186.5	32859911
AllCCS	[M+HCOO]-	186.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Huajiaosimuline	CC(C)C(=O)CCC1(C)OC2=C(C=C1)C(=O)N(C)C1=CC=CC=C21	3633.9	Standard polar	33892256
Huajiaosimuline	CC(C)C(=O)CCC1(C)OC2=C(C=C1)C(=O)N(C)C1=CC=CC=C21	2665.8	Standard non polar	33892256
Huajiaosimuline	CC(C)C(=O)CCC1(C)OC2=C(C=C1)C(=O)N(C)C1=CC=CC=C21	2789.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Huajiaosimuline,1TMS,isomer #1	CC(C)=C(CCC1(C)C=CC2=C(O1)C1=CC=CC=C1N(C)C2=O)O[Si](C)(C)C	2757.7	Semi standard non polar	33892256
Huajiaosimuline,1TMS,isomer #1	CC(C)=C(CCC1(C)C=CC2=C(O1)C1=CC=CC=C1N(C)C2=O)O[Si](C)(C)C	2559.2	Standard non polar	33892256
Huajiaosimuline,1TMS,isomer #2	CC(C)C(=CCC1(C)C=CC2=C(O1)C1=CC=CC=C1N(C)C2=O)O[Si](C)(C)C	2758.0	Semi standard non polar	33892256
Huajiaosimuline,1TMS,isomer #2	CC(C)C(=CCC1(C)C=CC2=C(O1)C1=CC=CC=C1N(C)C2=O)O[Si](C)(C)C	2541.0	Standard non polar	33892256
Huajiaosimuline,1TBDMS,isomer #1	CC(C)=C(CCC1(C)C=CC2=C(O1)C1=CC=CC=C1N(C)C2=O)O[Si](C)(C)C(C)(C)C	2991.9	Semi standard non polar	33892256
Huajiaosimuline,1TBDMS,isomer #1	CC(C)=C(CCC1(C)C=CC2=C(O1)C1=CC=CC=C1N(C)C2=O)O[Si](C)(C)C(C)(C)C	2761.4	Standard non polar	33892256
Huajiaosimuline,1TBDMS,isomer #2	CC(C)C(=CCC1(C)C=CC2=C(O1)C1=CC=CC=C1N(C)C2=O)O[Si](C)(C)C(C)(C)C	2980.4	Semi standard non polar	33892256
Huajiaosimuline,1TBDMS,isomer #2	CC(C)C(=CCC1(C)C=CC2=C(O1)C1=CC=CC=C1N(C)C2=O)O[Si](C)(C)C(C)(C)C	2742.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Huajiaosimuline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kkc-9771000000-3521ef3099ec156e202b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Huajiaosimuline 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 - Huajiaosimuline 10V, Positive-QTOF	splash10-004i-1119000000-4e1a0c88de5364699f05	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huajiaosimuline 20V, Positive-QTOF	splash10-0079-9631000000-9af853584dd968b58750	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huajiaosimuline 40V, Positive-QTOF	splash10-0abc-9600000000-a1c28ca84d960046f01d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huajiaosimuline 10V, Negative-QTOF	splash10-00di-0009000000-9ac77775a43f472df9ec	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huajiaosimuline 20V, Negative-QTOF	splash10-00di-2069000000-ecee5291100e33fdb6ec	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huajiaosimuline 40V, Negative-QTOF	splash10-0a59-4910000000-ffcdc4ba1ab5c204ce83	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huajiaosimuline 10V, Negative-QTOF	splash10-00di-0009000000-f0a5ade9142b21bf9f1f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huajiaosimuline 20V, Negative-QTOF	splash10-00fr-0096000000-52f814abe355844bb2df	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huajiaosimuline 40V, Negative-QTOF	splash10-01p2-1790000000-52d54800b18cb7caf2e1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huajiaosimuline 10V, Positive-QTOF	splash10-056r-0029000000-447ddb7c0e669c78aef9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huajiaosimuline 20V, Positive-QTOF	splash10-0006-0092000000-d4cbd1f8e6dfab5b4e06	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Huajiaosimuline 40V, Positive-QTOF	splash10-0ufr-1390000000-411af339aee7bead45e0	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB020099

KNApSAcK ID

C00037277

Chemspider ID

4476721

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318093

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1882881

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 Huajiaosimuline (HMDB0040369)

MOL for HMDB0040369 (Huajiaosimuline)

3D MOL for HMDB0040369 (Huajiaosimuline)

3D SDF for HMDB0040369 (Huajiaosimuline)

3D-SDF for HMDB0040369 (Huajiaosimuline)

PDB for HMDB0040369 (Huajiaosimuline)

3D PDB for HMDB0040369 (Huajiaosimuline)

SMILES for HMDB0040369 (Huajiaosimuline)

INCHI for HMDB0040369 (Huajiaosimuline)

Structure for HMDB0040369 (Huajiaosimuline)

3D Structure for HMDB0040369 (Huajiaosimuline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra