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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:52:03 UTC

Update Date

2022-11-23 21:39:02 UTC

HMDB ID

HMDB0243617

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol

Description

(4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol, also known as 3,4,4a,10b-tetrahydro-4-propyl-2H,5H-(1)benzopyrano(4,3-b)-1,4-oxazin-9-ol or PBPO, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. Based on a literature review a significant number of articles have been published on (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). (4ar,10br)-rel-4-propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0256149
     RDKit          3D
(4As,10bS)-4-propyl-3,4a,5,10b-tetrahydro-2H-chromeno[4,3-b][1,4]oxazin-9-ol
 37 39  0  0  0  0  0  0  0  0999 V2000
   -4.0206    0.5047    1.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8119    0.3134   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3465    0.5582   -0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543   -0.3442   -0.1188 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381   -1.7107   -0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4619   -2.0523   -1.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756   -1.1636   -1.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7588   -0.7480    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560   -0.0418    0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474   -0.7495    0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4607   -0.1165    0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6654   -0.8546    0.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4810    1.2561    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3093    1.9818   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0779    1.3257    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8672    1.9950   -0.0357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1815    1.4893    0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4007    0.0338    0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300    1.1764    1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9768    1.0827    1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0857   -0.4563    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1160   -0.7201   -0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4748    1.0035   -1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159    0.2518   -1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1040    1.6123   -0.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6068   -2.3765    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -1.8816   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7787   -1.9540   -2.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761   -3.1000   -1.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8593   -1.7211    0.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1740   -1.8340    0.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0656   -1.0424    1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4195    1.7702   -0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2978    3.0639   -0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0752    2.1298    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1649    1.6967    1.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833   -0.3784    1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  4  1  0
 18  8  1  0
 15  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
M  END

  Mrv1652309102122522D          

 18 20  0  0  0  0            999 V2000
    5.2520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0243617

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCN1CCOC2C1COC1=C2C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H19NO3/c1-2-5-15-6-7-17-14-11-8-10(16)3-4-13(11)18-9-12(14)15/h3-4,8,12,14,16H,2,5-7,9H2,1H3

> <INCHI_KEY>
YOILXOMTHPUMRG-UHFFFAOYSA-N

> <FORMULA>
C14H19NO3

> <MOLECULAR_WEIGHT>
249.31

> <EXACT_MASS>
249.136493476

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.745446001754196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-propyl-3,9-dioxa-6-azatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),11,13-trien-13-ol

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
2.062245090333334

> <ALOGPS_LOGS>
-1.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.764227235914307

> <JCHEM_PKA_STRONGEST_BASIC>
6.419378427295197

> <JCHEM_POLAR_SURFACE_AREA>
41.93000000000001

> <JCHEM_REFRACTIVITY>
68.76330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-propyl-3,9-dioxa-6-azatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),11,13-trien-13-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256149
     RDKit          3D
(4As,10bS)-4-propyl-3,4a,5,10b-tetrahydro-2H-chromeno[4,3-b][1,4]oxazin-9-ol
 37 39  0  0  0  0  0  0  0  0999 V2000
   -4.0206    0.5047    1.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8119    0.3134   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3465    0.5582   -0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543   -0.3442   -0.1188 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381   -1.7107   -0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4619   -2.0523   -1.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756   -1.1636   -1.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7588   -0.7480    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560   -0.0418    0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474   -0.7495    0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4607   -0.1165    0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6654   -0.8546    0.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4810    1.2561    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3093    1.9818   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0779    1.3257    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8672    1.9950   -0.0357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1815    1.4893    0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4007    0.0338    0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300    1.1764    1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9768    1.0827    1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0857   -0.4563    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1160   -0.7201   -0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4748    1.0035   -1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159    0.2518   -1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1040    1.6123   -0.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6068   -2.3765    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -1.8816   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7787   -1.9540   -2.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761   -3.1000   -1.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8593   -1.7211    0.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1740   -1.8340    0.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0656   -1.0424    1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4195    1.7702   -0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2978    3.0639   -0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0752    2.1298    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1649    1.6967    1.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833   -0.3784    1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  4  1  0
 18  8  1  0
 15  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
M  END

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       9.804   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       6.724   2.104   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.184  -0.564   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.874   3.437   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0243617
HETATM    1  C1  UNL     1       3.338   1.841   0.244  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.679   0.496  -0.236  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.841  -0.676   0.001  1.00  0.00           C  
HETATM    4  N1  UNL     1       1.509  -0.739  -0.493  1.00  0.00           N  
HETATM    5  C4  UNL     1       1.257  -2.245  -0.617  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.040  -2.502  -1.419  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.666  -1.282  -1.492  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.822  -0.887  -0.160  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.981   0.015   0.007  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.098  -0.104  -0.781  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.184   0.718  -0.616  1.00  0.00           C  
HETATM   12  O2  UNL     1      -5.293   0.554  -1.446  1.00  0.00           O  
HETATM   13  C10 UNL     1      -4.184   1.695   0.358  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.080   1.845   1.170  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.978   0.994   0.983  1.00  0.00           C  
HETATM   16  O3  UNL     1      -0.834   1.071   1.745  1.00  0.00           O  
HETATM   17  C13 UNL     1       0.429   0.929   1.043  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.450  -0.428   0.488  1.00  0.00           C  
HETATM   19  H1  UNL     1       2.574   2.385  -0.387  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.158   1.975   1.311  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.275   2.486   0.020  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.977   0.610  -1.330  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.714   0.254   0.219  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.431  -1.572  -0.407  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.871  -0.906   1.117  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.164  -2.693  -1.063  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.118  -2.568   0.420  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.247  -2.914  -2.437  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.665  -3.221  -0.951  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.134  -1.847   0.364  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.096  -0.879  -1.553  1.00  0.00           H  
HETATM   32  H14 UNL     1      -5.356   1.073  -2.331  1.00  0.00           H  
HETATM   33  H15 UNL     1      -5.030   2.352   0.507  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.014   2.586   1.951  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.484   1.675   0.251  1.00  0.00           H  
HETATM   36  H18 UNL     1       1.158   1.032   1.875  1.00  0.00           H  
HETATM   37  H19 UNL     1       0.702  -1.123   1.365  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   18
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8
CONECT    8    9   18   30
CONECT    9   10   10   15
CONECT   10   11   31
CONECT   11   12   13   13
CONECT   12   32
CONECT   13   14   33
CONECT   14   15   15   34
CONECT   15   16
CONECT   16   17
CONECT   17   18   35   36
CONECT   18   37
END

HMDB0256149
     RDKit          3D
(4As,10bS)-4-propyl-3,4a,5,10b-tetrahydro-2H-chromeno[4,3-b][1,4]oxazin-9-ol
 37 39  0  0  0  0  0  0  0  0999 V2000
   -4.0206    0.5047    1.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8119    0.3134   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3465    0.5582   -0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543   -0.3442   -0.1188 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381   -1.7107   -0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4619   -2.0523   -1.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756   -1.1636   -1.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7588   -0.7480    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560   -0.0418    0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474   -0.7495    0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4607   -0.1165    0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6654   -0.8546    0.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4810    1.2561    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3093    1.9818   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0779    1.3257    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8672    1.9950   -0.0357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1815    1.4893    0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4007    0.0338    0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300    1.1764    1.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9768    1.0827    1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0857   -0.4563    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1160   -0.7201   -0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4748    1.0035   -1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3159    0.2518   -1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1040    1.6123   -0.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6068   -2.3765    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -1.8816   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7787   -1.9540   -2.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761   -3.1000   -1.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8593   -1.7211    0.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1740   -1.8340    0.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0656   -1.0424    1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4195    1.7702   -0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2978    3.0639   -0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0752    2.1298    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1649    1.6967    1.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833   -0.3784    1.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  4  1  0
 18  8  1  0
 15  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3,4,4a,10b-Tetrahydro-4-propyl-2H,5H-(1)benzopyrano(4,3-b)-1,4-oxazin-9-ol	HMDB
3,4,4a,10b-Tetrahydro-4-propyl-2H,5H-(1)benzopyrano(4,3-b)-1,4-oxazin-9-ol, (+)-isomer	HMDB
3,4,4a,10b-Tetrahydro-4-propyl-2H,5H-(1)benzopyrano(4,3-b)-1,4-oxazin-9-ol, (-)-isomer	HMDB
PBPO	HMDB
PBTO	HMDB

Chemical Formula

C₁₄H₁₉NO₃

Average Molecular Weight

249.31

Monoisotopic Molecular Weight

249.136493476

IUPAC Name

6-propyl-3,9-dioxa-6-azatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),11,13-trien-13-ol

Traditional Name

6-propyl-3,9-dioxa-6-azatricyclo[8.4.0.0^{2,7}]tetradeca-1(10),11,13-trien-13-ol

CAS Registry Number

Not Available

SMILES

CCCN1CCOC2C1COC1=C2C=C(O)C=C1

InChI Identifier

InChI=1S/C14H19NO3/c1-2-5-15-6-7-17-14-11-8-10(16)3-4-13(11)18-9-12(14)15/h3-4,8,12,14,16H,2,5-7,9H2,1H3

InChI Key

YOILXOMTHPUMRG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Morpholine
Oxazinane
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Ether
Dialkyl ether
Oxacycle
Azacycle
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.79	ALOGPS
logP	2.06	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	6.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.93 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.76 m³·mol⁻¹	ChemAxon
Polarizability	27.75 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
DeepCCS	[M+H]+	153.809	30932474
DeepCCS	[M-H]-	151.451	30932474
DeepCCS	[M-2H]-	184.877	30932474
DeepCCS	[M+Na]+	159.903	30932474
AllCCS	[M+H]+	158.4	32859911
AllCCS	[M+H-H2O]+	154.6	32859911
AllCCS	[M+NH4]+	161.9	32859911
AllCCS	[M+Na]+	163.0	32859911
AllCCS	[M-H]-	163.0	32859911
AllCCS	[M+Na-2H]-	162.9	32859911
AllCCS	[M+HCOO]-	162.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(4Ar,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol	CCCN1CCOC2C1COC1=C2C=C(O)C=C1	2112.5	Standard non polar	33892256
(4Ar,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol	CCCN1CCOC2C1COC1=C2C=C(O)C=C1	2112.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00vl-5890000000-0688cdd90cea7be45b82	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol 10V, Positive-QTOF	splash10-0udi-0090000000-64a916db98d266c25eb8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol 20V, Positive-QTOF	splash10-0udi-0090000000-9dbcd120e62477a572c4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol 40V, Positive-QTOF	splash10-0zfs-1930000000-853dfda5362ac158def8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol 10V, Negative-QTOF	splash10-0002-0090000000-207446aa3d61457b6f3e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol 20V, Negative-QTOF	splash10-0002-0090000000-5a4f9a4bc3a851701c18	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol 40V, Negative-QTOF	splash10-0a4i-0950000000-a7bf5d938b16312270df	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4936

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5117

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol (HMDB0243617)

MOL for HMDB0243617 ((4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol)

3D MOL for HMDB0243617 ((4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol)

3D SDF for HMDB0243617 ((4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol)

3D-SDF for HMDB0243617 ((4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol)

PDB for HMDB0243617 ((4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol)

3D PDB for HMDB0243617 ((4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol)

SMILES for HMDB0243617 ((4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol)

INCHI for HMDB0243617 ((4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol)

Structure for HMDB0243617 ((4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol)

3D Structure for HMDB0243617 ((4aR,10bR)-rel-4-Propyl-2,3,4,4a,5,10b-hexahydrochromeno[4,3-b][1,4]oxazin-9-ol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra