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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-28 15:22:06 UTC

Update Date

2021-09-26 22:35:32 UTC

HMDB ID

HMDB0242200

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane

Description

(-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane, also known as MR 1452 MS or furylmethylnormetazocine, belongs to the class of organic compounds known as 2,6-dimethyl-3-benzazocines. These are aromatic compounds containing a 6,7-benzomorphan skeleton, which is substituted by methyl group at the 2- and 6-positions. Based on a literature review very few articles have been published on (-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane. This compound has been identified in human blood as reported by (PMID: 31557052 ). (-)-alpha-5,9-dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane 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

HMDB0242200
     RDKit          3D
(-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane
 45 48  0  0  0  0  0  0  0  0999 V2000
    1.4097   -2.4410    1.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4800   -1.7732    0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4773   -0.8791    0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2606    0.0777    1.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4359    0.6870    1.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960    1.7349    1.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1891    2.3288    1.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103    1.8693   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7225    2.4733   -0.6514 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657    0.8410   -0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8446    0.2218   -0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1786   -0.8820   -0.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2397   -1.6934   -1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1868   -0.3599   -1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854   -0.1540   -1.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3738   -0.1530    0.0454 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7364   -0.4824    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7223    0.4553   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2195    1.6171    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    2.1554   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1832    1.3580   -1.5329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3542    0.3343   -1.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0952   -1.6961    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9335   -3.3009    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7675   -2.8498    1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1232   -2.5305   -0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0345   -1.5776    1.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4257    0.9074    2.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5730   -0.4424    2.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215    2.0668    2.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7270    3.1425    1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0498    2.1522   -1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2870    0.4729   -1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8098   -2.7095   -1.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4546   -1.2748   -2.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1316   -1.7744   -0.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1892   -1.0703   -2.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220    0.5883   -2.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8749   -0.9066   -1.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5562    0.8346   -1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9073   -1.5360    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -0.5196    1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9600    2.0433    1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7066    3.0848   -0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2402   -0.4402   -2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  6  7  1  0
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 22 45  1  0
M  END


  Mrv1652308282117322D          

 22 25  0  0  0  0            999 V2000
    2.2581    0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717    0.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760   -0.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6989   -0.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389    0.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797    1.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    1.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332    1.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931    0.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    0.1662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853   -0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1741    0.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9463   -0.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4612    0.6049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0072    1.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2117    1.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    2.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8628    1.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6050    1.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9811   -0.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    1.6971    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
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  2  7  1  0  0  0  0
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  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
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 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
  7 17  1  0  0  0  0
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 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  5 21  1  0  0  0  0
 19 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242200

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CC3=C(C=C(O)C=C3)C1(C)CCN2CC1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO2/c1-13-18-9-15-3-4-16(21)10-17(15)19(13,2)6-7-20(18)11-14-5-8-22-12-14/h3-5,8,10,12-13,18,21H,6-7,9,11H2,1-2H3

> <INCHI_KEY>
MSBGXQSDBDHIGV-UHFFFAOYSA-N

> <FORMULA>
C19H23NO2

> <MOLECULAR_WEIGHT>
297.398

> <EXACT_MASS>
297.172878985

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.33255591387746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-[(furan-3-yl)methyl]-1,13-dimethyl-10-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-4-ol

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
3.506404347259902

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.335884890016754

> <JCHEM_PKA_STRONGEST_BASIC>
9.260520868976036

> <JCHEM_POLAR_SURFACE_AREA>
36.61

> <JCHEM_REFRACTIVITY>
87.80710000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-(furan-3-ylmethyl)-1,13-dimethyl-10-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-4-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0242200
     RDKit          3D
(-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane
 45 48  0  0  0  0  0  0  0  0999 V2000
    1.4097   -2.4410    1.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4800   -1.7732    0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4773   -0.8791    0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2606    0.0777    1.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4359    0.6870    1.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960    1.7349    1.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1891    2.3288    1.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103    1.8693   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7225    2.4733   -0.6514 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657    0.8410   -0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8446    0.2218   -0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1786   -0.8820   -0.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2397   -1.6934   -1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1868   -0.3599   -1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854   -0.1540   -1.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3738   -0.1530    0.0454 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7364   -0.4824    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7223    0.4553   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2195    1.6171    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    2.1554   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1832    1.3580   -1.5329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3542    0.3343   -1.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0952   -1.6961    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9335   -3.3009    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7675   -2.8498    1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1232   -2.5305   -0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0345   -1.5776    1.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4257    0.9074    2.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5730   -0.4424    2.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215    2.0668    2.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7270    3.1425    1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0498    2.1522   -1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2870    0.4729   -1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8098   -2.7095   -1.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4546   -1.2748   -2.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1316   -1.7744   -0.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1892   -1.0703   -2.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220    0.5883   -2.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8749   -0.9066   -1.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5562    0.8346   -1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9073   -1.5360    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -0.5196    1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9600    2.0433    1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7066    3.0848   -0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2402   -0.4402   -2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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  4  5  1  0
  5  6  2  0
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  8 10  1  0
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 12 14  1  0
 14 15  1  0
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 18 19  1  0
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 21 22  1  0
 12  2  1  0
 22 18  2  0
 16  3  1  0
 11  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
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  4 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 13 34  1  0
 13 35  1  0
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 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 22 45  1  0
M  END

HEADER    PROTEIN                                 28-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-AUG-21         0                                  
HETATM    1  C   UNK     0       4.215   1.519   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.747   1.053   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.635  -0.698   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.171  -0.587   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.179   0.577   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.069   2.113   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.905   3.121   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.369   3.011   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.361   1.846   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.471   0.310   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.906  -0.380   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.192   0.468   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.633  -0.074   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.594   1.129   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.747   2.415   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.262   2.006   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.390   4.582   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.344   2.977   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.729   2.304   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.840   0.768   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.565  -0.096   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.004   3.168   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    2    8   17                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17    7                                                            
CONECT   18    6   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20    5                                                       
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0254920
HETATM    1  C1  UNL     1      -0.315  -2.703  -1.946  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.717  -1.385  -1.432  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.298  -0.283  -1.634  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.420   1.039  -1.558  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.505   1.067  -0.581  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.193   2.293  -0.427  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.220   2.394   0.469  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.579   1.303   1.216  1.00  0.00           C  
HETATM    9  O1  UNL     1      -4.638   1.427   2.132  1.00  0.00           O  
HETATM   10  C9  UNL     1      -2.902   0.119   1.055  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.860  -0.026   0.163  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.143  -1.312   0.006  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.022  -2.489   0.380  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.012  -1.296   0.974  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.367  -1.267   0.310  1.00  0.00           C  
HETATM   16  N1  UNL     1       1.352  -0.285  -0.700  1.00  0.00           N  
HETATM   17  C15 UNL     1       2.557   0.366  -1.035  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.189   1.138   0.060  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.482   1.617  -0.038  1.00  0.00           C  
HETATM   20  C18 UNL     1       4.735   2.281   1.141  1.00  0.00           C  
HETATM   21  O2  UNL     1       3.665   2.204   1.893  1.00  0.00           O  
HETATM   22  C19 UNL     1       2.723   1.528   1.277  1.00  0.00           C  
HETATM   23  H1  UNL     1       0.023  -3.459  -1.251  1.00  0.00           H  
HETATM   24  H2  UNL     1      -1.114  -3.191  -2.579  1.00  0.00           H  
HETATM   25  H3  UNL     1       0.531  -2.547  -2.680  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.622  -1.056  -2.029  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.731  -0.408  -2.669  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.815   1.301  -2.584  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.295   1.884  -1.342  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.920   3.160  -1.009  1.00  0.00           H  
HETATM   31  H9  UNL     1      -3.782   3.328   0.621  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.394   1.713   3.064  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.175  -0.731   1.631  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.162  -2.492   1.481  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.444  -3.409   0.154  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.982  -2.449  -0.178  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.027  -2.152   1.677  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.008  -0.386   1.646  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.698  -2.274  -0.020  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.100  -0.978   1.092  1.00  0.00           H  
HETATM   41  H19 UNL     1       3.325  -0.304  -1.499  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.323   1.115  -1.841  1.00  0.00           H  
HETATM   43  H21 UNL     1       5.179   1.504  -0.871  1.00  0.00           H  
HETATM   44  H22 UNL     1       5.657   2.800   1.445  1.00  0.00           H  
HETATM   45  H23 UNL     1       1.716   1.302   1.662  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   12   26
CONECT    3    4   16   27
CONECT    4    5   28   29
CONECT    5    6    6   11
CONECT    6    7   30
CONECT    7    8    8   31
CONECT    8    9   10
CONECT    9   32
CONECT   10   11   11   33
CONECT   11   12
CONECT   12   13   14
CONECT   13   34   35   36
CONECT   14   15   37   38
CONECT   15   16   39   40
CONECT   16   17
CONECT   17   18   41   42
CONECT   18   19   22   22
CONECT   19   20   20   43
CONECT   20   21   44
CONECT   21   22
CONECT   22   45
END

HMDB0242200
     RDKit          3D
(-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane
 45 48  0  0  0  0  0  0  0  0999 V2000
    1.4097   -2.4410    1.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4800   -1.7732    0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4773   -0.8791    0.8615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2606    0.0777    1.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4359    0.6870    1.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960    1.7349    1.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1891    2.3288    1.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103    1.8693   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7225    2.4733   -0.6514 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657    0.8410   -0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8446    0.2218   -0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1786   -0.8820   -0.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2397   -1.6934   -1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1868   -0.3599   -1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854   -0.1540   -1.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3738   -0.1530    0.0454 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7364   -0.4824    0.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7223    0.4553   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2195    1.6171    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    2.1554   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1832    1.3580   -1.5329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3542    0.3343   -1.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0952   -1.6961    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9335   -3.3009    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7675   -2.8498    1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1232   -2.5305   -0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0345   -1.5776    1.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4257    0.9074    2.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5730   -0.4424    2.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215    2.0668    2.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7270    3.1425    1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0498    2.1522   -1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2870    0.4729   -1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8098   -2.7095   -1.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4546   -1.2748   -2.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1316   -1.7744   -0.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1892   -1.0703   -2.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220    0.5883   -2.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8749   -0.9066   -1.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5562    0.8346   -1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9073   -1.5360    0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -0.5196    1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9600    2.0433    1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7066    3.0848   -0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2402   -0.4402   -2.0958 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 12  2  1  0
 22 18  2  0
 16  3  1  0
 11  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 19 43  1  0
 20 44  1  0
 22 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-a-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane	Generator
(-)-Α-5,9-dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane	Generator
alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphan	HMDB
MR 1452 MS	HMDB
MR 1452, (2R-(2alpha,6alpha,11R*))-isomer	HMDB
MR 1452, (2S-(2alpha,6alpha,11R*))-isomer	HMDB
MR 1452, (2alpha,6alpha,11R*)-isomer	HMDB
Furylmethylnormetazocine	HMDB
MR 1452 Methanefulfonate, (2S-(2alpha,6alpha,11R*))-isomer	HMDB
MR 1452, (2alpha,6alpha,11R*)-(+-)-isomer	HMDB
MR 1452 Methanefulfonate, (2R-(2alpha,6alpha,11R*))-isomer	HMDB

Chemical Formula

C₁₉H₂₃NO₂

Average Molecular Weight

297.398

Monoisotopic Molecular Weight

297.172878985

IUPAC Name

10-[(furan-3-yl)methyl]-1,13-dimethyl-10-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-4-ol

Traditional Name

10-(furan-3-ylmethyl)-1,13-dimethyl-10-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-4-ol

CAS Registry Number

Not Available

SMILES

CC1C2CC3=C(C=C(O)C=C3)C1(C)CCN2CC1=COC=C1

InChI Identifier

InChI=1S/C19H23NO2/c1-13-18-9-15-3-4-16(21)10-17(15)19(13,2)6-7-20(18)11-14-5-8-22-12-14/h3-5,8,10,12-13,18,21H,6-7,9,11H2,1-2H3

InChI Key

MSBGXQSDBDHIGV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,6-dimethyl-3-benzazocines. These are aromatic compounds containing a 6,7-benzomorphan skeleton, which is substituted by methyl group at the 2- and 6-positions.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

6,7-benzomorphans

Sub Class

2,6-dimethyl-3-benzazocines

Direct Parent

2,6-dimethyl-3-benzazocines

Alternative Parents

Substituents

2,6-dimethyl-3-benzazocine
4-hydroxy-6,7-benzomorphan
Benzazocine
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Benzenoid
Furan
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
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	4.02	ALOGPS
logP	3.51	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	10.34	ChemAxon
pKa (Strongest Basic)	9.26	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	36.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	87.81 m³·mol⁻¹	ChemAxon
Polarizability	33.33 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	176.596	30932474
DeepCCS	[M-H]-	174.238	30932474
DeepCCS	[M-2H]-	207.125	30932474
DeepCCS	[M+Na]+	182.69	30932474
AllCCS	[M+H]+	173.4	32859911
AllCCS	[M+H-H2O]+	170.1	32859911
AllCCS	[M+NH4]+	176.5	32859911
AllCCS	[M+Na]+	177.4	32859911
AllCCS	[M-H]-	179.1	32859911
AllCCS	[M+Na-2H]-	178.7	32859911
AllCCS	[M+HCOO]-	178.4	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.	4.02 minutes	32390414
Predicted by Siyang on May 30, 2022	10.5253 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.27 minutes	32390414

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane,1TMS,isomer #1	CC1C2CC3=CC=C(O[Si](C)(C)C)C=C3C1(C)CCN2CC1=COC=C1	2452.3	Semi standard non polar	33892256
(-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane,1TMS,isomer #1	CC1C2CC3=CC=C(O[Si](C)(C)C)C=C3C1(C)CCN2CC1=COC=C1	2512.0	Standard non polar	33892256
(-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane,1TMS,isomer #1	CC1C2CC3=CC=C(O[Si](C)(C)C)C=C3C1(C)CCN2CC1=COC=C1	2810.5	Standard polar	33892256
(-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane,1TBDMS,isomer #1	CC1C2CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3C1(C)CCN2CC1=COC=C1	2709.6	Semi standard non polar	33892256
(-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane,1TBDMS,isomer #1	CC1C2CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3C1(C)CCN2CC1=COC=C1	2757.4	Standard non polar	33892256
(-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane,1TBDMS,isomer #1	CC1C2CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3C1(C)CCN2CC1=COC=C1	2950.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-5690000000-d14dbbac7294fd2fe8b0	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane 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 - (-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane 10V, Positive-QTOF	splash10-0002-0090000000-480fa4cd309c1b6ae4dc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane 20V, Positive-QTOF	splash10-0002-0090000000-39f98ea5968af4f1912b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane 40V, Positive-QTOF	splash10-003r-5950000000-a83d8282bdee6d8e1e2f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane 10V, Negative-QTOF	splash10-0002-0090000000-ede096e7f2163d95f8ea	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane 20V, Negative-QTOF	splash10-000t-9080000000-0da0daa361cb7b3eb624	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane 40V, Negative-QTOF	splash10-03xr-3190000000-bded22b00c43f76ce245	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

381465

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

431327

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 (-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane (HMDB0242200)

MOL for HMDB0242200 ((-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane)

3D MOL for HMDB0242200 ((-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane)

3D SDF for HMDB0242200 ((-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane)

3D-SDF for HMDB0242200 ((-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane)

PDB for HMDB0242200 ((-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane)

3D PDB for HMDB0242200 ((-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane)

SMILES for HMDB0242200 ((-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane)

INCHI for HMDB0242200 ((-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane)

Structure for HMDB0242200 ((-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane)

3D Structure for HMDB0242200 ((-)-alpha-5,9-Dimethyl-2-(3-furylmethyl)-2'-hydroxy-6,7-benzomorphane)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra