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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:24:01 UTC

Update Date

2022-09-22 17:45:01 UTC

HMDB ID

HMDB0250396

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dihydroneopine

Description

10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-ol belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. Based on a literature review very few articles have been published on 10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dihydroneopine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dihydroneopine 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

HMDB0251317
     RDKit          3D
Dihydroisocodeine
 45 49  0  0  0  0  0  0  0  0999 V2000
    5.3700   -1.1970   -0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2368   -0.4064   -0.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947   -0.8539   -0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7736   -2.1926   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5011   -2.6373    0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4629   -1.7291    0.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7828   -0.4570    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9634    0.0823   -0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7743    1.4635   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7122    1.7960    0.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0733    2.9820    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6767    4.1234    0.4899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255    2.9570    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9572    1.6710    1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915    0.4750    1.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893   -0.8444    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9040   -2.0094    0.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6466   -0.5837   -0.1151 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7056   -1.5387   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8468   -0.4761   -1.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460    0.7288   -1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934    0.6122    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5706   -1.4682   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2485   -0.5800   -0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3880   -2.0977   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5344   -2.9417   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3026   -3.6702    0.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243    1.7639    1.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2837    3.1527   -0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6069    3.9809    0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1339    3.5338    1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0777    3.5961    0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7983    1.4666    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4766    1.7629    2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5060    0.4228    2.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4699   -1.0495    1.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8013   -2.5902    1.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3522   -2.7386    0.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5776   -1.1316    0.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3931   -2.5252    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0469   -1.5913   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2602   -1.3854   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5331   -0.3029   -2.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6002    1.6202   -1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2339    0.8073   -2.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 10  1  0
 17  6  1  0
 22  7  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
M  END


  Mrv1533004181501352D          

 22 26  0  0  0  0            999 V2000
    3.9875    3.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4883    3.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1710    2.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6911    1.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3796    1.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5548    0.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2560    0.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4373    0.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476    0.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8732    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5605    1.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1194    2.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8640    3.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9453    2.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6109    2.8048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225    2.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320    1.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602    1.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3150    0.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1725   -0.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8937   -0.3996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0314   -1.2130    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  2  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250396

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2CC3C4CCC(O)C5OC1=C2C45CCN3C

> <INCHI_IDENTIFIER>
InChI=1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3

> <INCHI_KEY>
RBOXVHNMENFORY-UHFFFAOYSA-N

> <FORMULA>
C18H23NO3

> <MOLECULAR_WEIGHT>
301.386

> <EXACT_MASS>
301.167793605

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.79856722814689

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18)-trien-14-ol

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.5489654796666665

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.15155112831567

> <JCHEM_PKA_STRONGEST_BASIC>
9.331082819397679

> <JCHEM_POLAR_SURFACE_AREA>
41.93

> <JCHEM_REFRACTIVITY>
83.6421

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-dihydrocodeine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251317
     RDKit          3D
Dihydroisocodeine
 45 49  0  0  0  0  0  0  0  0999 V2000
    5.3700   -1.1970   -0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2368   -0.4064   -0.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947   -0.8539   -0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7736   -2.1926   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5011   -2.6373    0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4629   -1.7291    0.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7828   -0.4570    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9634    0.0823   -0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7743    1.4635   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7122    1.7960    0.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0733    2.9820    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6767    4.1234    0.4899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255    2.9570    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9572    1.6710    1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915    0.4750    1.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893   -0.8444    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9040   -2.0094    0.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6466   -0.5837   -0.1151 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7056   -1.5387   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8468   -0.4761   -1.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460    0.7288   -1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934    0.6122    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5706   -1.4682   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2485   -0.5800   -0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3880   -2.0977   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5344   -2.9417   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3026   -3.6702    0.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243    1.7639    1.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2837    3.1527   -0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6069    3.9809    0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1339    3.5338    1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0777    3.5961    0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7983    1.4666    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4766    1.7629    2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5060    0.4228    2.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4699   -1.0495    1.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8013   -2.5902    1.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3522   -2.7386    0.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5776   -1.1316    0.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3931   -2.5252    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0469   -1.5913   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2602   -1.3854   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5331   -0.3029   -2.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6002    1.6202   -1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2339    0.8073   -2.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 10  1  0
 17  6  1  0
 22  7  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
M  END

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       7.443   7.229   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.378   6.005   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.786   4.584   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.757   3.359   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.175   1.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.636   1.769   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.078   0.371   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.550   0.352   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.449   1.818   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.630   2.092   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.046   3.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.090   4.596   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.613   6.061   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.631   4.297   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.874   5.236   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.202   4.408   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.660   2.975   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.032   2.745   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.455   1.628   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.189  -0.029   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.535  -0.746   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       3.792  -2.264   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15    3   17                                                  
CONECT   17   16    6   18                                                  
CONECT   18   17    9   14   19                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    8   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

COMPND    HMDB0251317
HETATM    1  C1  UNL     1       5.370  -1.197  -0.981  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.237  -0.406  -0.834  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.995  -0.854  -0.436  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.774  -2.193  -0.138  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.501  -2.637   0.269  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.463  -1.729   0.371  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.783  -0.457   0.057  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.963   0.082  -0.340  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.774   1.464  -0.532  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.712   1.796   0.367  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.073   2.982   0.118  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.677   4.123   0.490  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.326   2.957   0.933  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.957   1.671   1.258  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.091   0.475   1.300  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.789  -0.844   1.045  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.904  -2.009   0.835  1.00  0.00           C  
HETATM   18  N1  UNL     1      -2.647  -0.584  -0.115  1.00  0.00           N  
HETATM   19  C15 UNL     1      -3.706  -1.539  -0.231  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.847  -0.476  -1.321  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.946   0.729  -1.179  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.193   0.612   0.083  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.571  -1.468  -2.051  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.249  -0.580  -0.630  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.388  -2.098  -0.321  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.534  -2.942  -0.199  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.303  -3.670   0.506  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.124   1.764   1.378  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.284   3.153  -0.977  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.607   3.981   0.158  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.134   3.534   1.886  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.078   3.596   0.382  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.798   1.467   0.531  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.477   1.763   2.246  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.506   0.423   2.219  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.470  -1.049   1.892  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.801  -2.590   1.796  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.352  -2.739   0.119  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.578  -1.132   0.358  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.393  -2.525   0.172  1.00  0.00           H  
HETATM   41  H19 UNL     1      -4.047  -1.591  -1.287  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.260  -1.385  -1.511  1.00  0.00           H  
HETATM   43  H21 UNL     1      -2.533  -0.303  -2.156  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.600   1.620  -1.253  1.00  0.00           H  
HETATM   45  H23 UNL     1      -0.234   0.807  -2.028  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   17
CONECT    7    8    8   22
CONECT    8    9
CONECT    9   10
CONECT   10   11   22   28
CONECT   11   12   13   29
CONECT   12   30
CONECT   13   14   31   32
CONECT   14   15   33   34
CONECT   15   16   22   35
CONECT   16   17   18   36
CONECT   17   37   38
CONECT   18   19   20
CONECT   19   39   40   41
CONECT   20   21   42   43
CONECT   21   22   44   45
END

HMDB0251317
     RDKit          3D
Dihydroisocodeine
 45 49  0  0  0  0  0  0  0  0999 V2000
    5.3700   -1.1970   -0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2368   -0.4064   -0.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947   -0.8539   -0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7736   -2.1926   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5011   -2.6373    0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4629   -1.7291    0.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7828   -0.4570    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9634    0.0823   -0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7743    1.4635   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7122    1.7960    0.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0733    2.9820    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6767    4.1234    0.4899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255    2.9570    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9572    1.6710    1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915    0.4750    1.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893   -0.8444    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9040   -2.0094    0.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6466   -0.5837   -0.1151 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7056   -1.5387   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8468   -0.4761   -1.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460    0.7288   -1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934    0.6122    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5706   -1.4682   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2485   -0.5800   -0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3880   -2.0977   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5344   -2.9417   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3026   -3.6702    0.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243    1.7639    1.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2837    3.1527   -0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6069    3.9809    0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1339    3.5338    1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0777    3.5961    0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7983    1.4666    0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4766    1.7629    2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5060    0.4228    2.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4699   -1.0495    1.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8013   -2.5902    1.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3522   -2.7386    0.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5776   -1.1316    0.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3931   -2.5252    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0469   -1.5913   -1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2602   -1.3854   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5331   -0.3029   -2.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6002    1.6202   -1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2339    0.8073   -2.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 10  1  0
 17  6  1  0
 22  7  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Paracodin	MeSH
Tiamon	MeSH
Dihydrocodeine acetate, (5alpha,6alpha)-isomer	MeSH
Dihydrocodeine tartrate (1:1), (5alpha,6alpha)-(R-(r,r))-isomer	MeSH
DHC Continus	MeSH
Tosidrin	MeSH
Dihydrocodeine bitartrate	MeSH
Dihydrocodeine phosphate (1:1), (5alpha,6alpha)-isomer	MeSH
Dihydrocodeine, (5alpha,6alpha,14alpha)-isomer	MeSH
Dihydrocodeine, thiocyanate salt (5alpha,6alpha)-isomer	MeSH
DHC Mundipharma	MeSH
Dicodin	MeSH
Rikodeine	MeSH
Dihydrocodeine, (5alpha,6beta,14alpha)-isomer	MeSH
Paramol 118	MeSH
Contugesic	MeSH
Paracodina	MeSH
Dihydrocodeine	MeSH
Dihydrocodeine hydrochloride, (5alpha,6alpha)-isomer	MeSH
Dihydrocodeine tartrate (1:1), (5alpha,6beta)-(R-(r,r))-isomer	MeSH
Dihydrocodeine, (5alpha,6beta)-isomer	MeSH

Chemical Formula

C₁₈H₂₃NO₃

Average Molecular Weight

301.386

Monoisotopic Molecular Weight

301.167793605

IUPAC Name

10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18)-trien-14-ol

Traditional Name

(-)-dihydrocodeine

CAS Registry Number

Not Available

SMILES

COC1=CC=C2CC3C4CCC(O)C5OC1=C2C45CCN3C

InChI Identifier

InChI=1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3

InChI Key

RBOXVHNMENFORY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Morphinans

Sub Class

Not Available

Direct Parent

Morphinans

Alternative Parents

Substituents

Morphinan
Phenanthrene
Tetralin
Coumaran
Anisole
Alkyl aryl ether
Aralkylamine
Piperidine
Benzenoid
Cyclic alcohol
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Organopnictogen compound
Organooxygen compound
Organic nitrogen compound
Amine
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)

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	1.58	ALOGPS
logP	1.55	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	14.15	ChemAxon
pKa (Strongest Basic)	9.33	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.93 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.64 m³·mol⁻¹	ChemAxon
Polarizability	32.8 Å³	ChemAxon
Number of Rings	5	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-2H]-	206.059	30932474
DeepCCS	[M+Na]+	181.601	30932474
AllCCS	[M+H]+	174.3	32859911
AllCCS	[M+H-H2O]+	171.2	32859911
AllCCS	[M+NH4]+	177.2	32859911
AllCCS	[M+Na]+	178.0	32859911
AllCCS	[M-H]-	176.7	32859911
AllCCS	[M+Na-2H]-	176.3	32859911
AllCCS	[M+HCOO]-	176.0	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydroneopine,1TMS,isomer #1	COC1=CC=C2CC3C4CCC(O[Si](C)(C)C)C5OC1=C2C45CCN3C	2412.7	Semi standard non polar	33892256
Dihydroneopine,1TMS,isomer #1	COC1=CC=C2CC3C4CCC(O[Si](C)(C)C)C5OC1=C2C45CCN3C	2425.6	Standard non polar	33892256
Dihydroneopine,1TMS,isomer #1	COC1=CC=C2CC3C4CCC(O[Si](C)(C)C)C5OC1=C2C45CCN3C	3033.7	Standard polar	33892256
Dihydroneopine,1TBDMS,isomer #1	COC1=CC=C2CC3C4CCC(O[Si](C)(C)C(C)(C)C)C5OC1=C2C45CCN3C	2654.5	Semi standard non polar	33892256
Dihydroneopine,1TBDMS,isomer #1	COC1=CC=C2CC3C4CCC(O[Si](C)(C)C(C)(C)C)C5OC1=C2C45CCN3C	2711.8	Standard non polar	33892256
Dihydroneopine,1TBDMS,isomer #1	COC1=CC=C2CC3C4CCC(O[Si](C)(C)C(C)(C)C)C5OC1=C2C45CCN3C	3198.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroneopine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0553-3090000000-7f13a46ab6069c52a49b	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroneopine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroneopine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydroneopine 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 - Dihydroneopine 10V, Positive-QTOF	splash10-0udi-0009000000-f31fdc0a643a184ad00a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroneopine 20V, Positive-QTOF	splash10-0udi-0009000000-3d9d5ffc3b6cc1754f10	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroneopine 40V, Positive-QTOF	splash10-0zml-1092000000-2871c42a433aabbe7088	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroneopine 10V, Negative-QTOF	splash10-0udi-0009000000-d8889aea2cbe8e49784e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroneopine 20V, Negative-QTOF	splash10-0udi-0009000000-d8889aea2cbe8e49784e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydroneopine 40V, Negative-QTOF	splash10-0002-0091000000-fe84360fc652b7465fa8	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	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

2955

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3063

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 Dihydroneopine (HMDB0250396)

MOL for HMDB0250396 (Dihydroneopine)

3D MOL for HMDB0250396 (Dihydroneopine)

3D SDF for HMDB0250396 (Dihydroneopine)

3D-SDF for HMDB0250396 (Dihydroneopine)

PDB for HMDB0250396 (Dihydroneopine)

3D PDB for HMDB0250396 (Dihydroneopine)

SMILES for HMDB0250396 (Dihydroneopine)

INCHI for HMDB0250396 (Dihydroneopine)

Structure for HMDB0250396 (Dihydroneopine)

3D Structure for HMDB0250396 (Dihydroneopine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra