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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-08-13 01:15:00 UTC

Update Date

2021-09-14 15:48:20 UTC

HMDB ID

HMDB0003601

Secondary Accession Numbers

HMDB03601

Metabolite Identification

Common Name

(S)-Reticuline

Description

(S)-Reticuline is an endogenous precursor of morphine (PMID: 15383669 ). (S)-Reticuline is a key intermediate in the synthesis of morphine, the major active metabolite of the opium poppy. "Endogenous morphine" has been long isolated and authenticated by mass spectrometry in trace amounts from animal- and human-specific tissue or fluids (PMID: 15874902 ). Human neuroblastoma cells (SH-SY5Y) were shown capable of synthesizing morphine as well. (S)-Reticuline undergoes a change of configuration at C-1 during its transformation into salutaridinol and thebaine. From thebaine, there is a bifurcate pathway leading to morphine proceeding via codeine or oripavine, in both plants and mammals (PMID 15937106 ).

Structure

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

HMDB0003601
     RDKit          3D
(S)-Reticuline
 47 49  0  0  0  0  0  0  0  0999 V2000
    5.6741    0.3907   -2.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8805    1.2798   -1.7268 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019    0.8021   -0.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6759   -0.5403   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7152   -0.9632    0.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121   -0.1070    0.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433   -0.6752    1.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750   -1.1068    1.4335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3419   -0.2063    0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3166    1.1798    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2517    2.0143    0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1426    3.3961    0.6243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2723    1.4591   -0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2193    2.2734   -0.8606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3048    1.7933   -1.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3492    0.1127   -0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903   -0.7145    0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5989   -2.1782   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296   -2.9578    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -2.1945    0.4152 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0651   -1.6731   -0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570    1.2190    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1387    1.6803   -0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3830    3.0350   -0.2870 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3518   -0.1604   -1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170   -0.3969   -2.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2632    0.9021   -3.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2817   -1.2360   -1.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -2.0301    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4642   -1.5997    2.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8342   -0.0535    2.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8794   -1.6365    2.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248    1.5516    1.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111    3.8206    1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7642    0.9456   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1043    2.5330   -1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9969    1.3586   -2.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573   -0.3084   -1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5015   -2.4931    0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332   -2.4366   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6754   -3.2074    1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3518   -3.9360   -0.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7512   -2.1543   -1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9793   -1.8617   -1.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078   -0.5797   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6434    1.9825    1.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8191    3.6776    0.2546 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  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  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  6 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 20  8  1  0
 17  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  1
 10 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 24 47  1  0
M  END


  Mrv1652307152023352D          

 24 26  0  0  0  0            999 V2000
10000.075710000.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5030 9999.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.507110002.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2235 9999.1791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.934410001.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2235 9997.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.650110001.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3698 9998.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.219610001.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.505110001.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.790610001.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.790510000.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.505010000.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.219610000.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6505 9999.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9359 9998.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9359 9997.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6504 9997.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0760 9999.1750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3615 9998.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3615 9997.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0760 9997.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7905 9997.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7905 9998.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14  9  1  0  0  0  0
  1 12  1  0  0  0  0
 10  3  1  0  0  0  0
  9  5  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 16  4  1  0  0  0  0
 17  6  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
 23 24  1  0  0  0  0
 19  1  1  6  0  0  0
 24  2  1  0  0  0  0
 20 15  2  0  0  0  0
 18 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003601

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(O)C=C23)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1

> <INCHI_KEY>
BHLYRWXGMIUIHG-HNNXBMFYSA-N

> <FORMULA>
C19H23NO4

> <MOLECULAR_WEIGHT>
329.3902

> <EXACT_MASS>
329.162708229

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
36.14650233241288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
3.1049593069999997

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.36995691314734

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.763064568264014

> <JCHEM_PKA_STRONGEST_BASIC>
7.810592585816691

> <JCHEM_POLAR_SURFACE_AREA>
62.160000000000004

> <JCHEM_REFRACTIVITY>
93.83630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+,-)-reticuline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003601
     RDKit          3D
(S)-Reticuline
 47 49  0  0  0  0  0  0  0  0999 V2000
    5.6741    0.3907   -2.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8805    1.2798   -1.7268 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019    0.8021   -0.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6759   -0.5403   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7152   -0.9632    0.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121   -0.1070    0.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433   -0.6752    1.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750   -1.1068    1.4335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3419   -0.2063    0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3166    1.1798    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2517    2.0143    0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1426    3.3961    0.6243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2723    1.4591   -0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2193    2.2734   -0.8606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3048    1.7933   -1.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3492    0.1127   -0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903   -0.7145    0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5989   -2.1782   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296   -2.9578    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -2.1945    0.4152 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0651   -1.6731   -0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570    1.2190    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1387    1.6803   -0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3830    3.0350   -0.2870 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3518   -0.1604   -1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170   -0.3969   -2.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2632    0.9021   -3.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2817   -1.2360   -1.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -2.0301    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4642   -1.5997    2.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8342   -0.0535    2.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8794   -1.6365    2.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248    1.5516    1.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111    3.8206    1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7642    0.9456   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1043    2.5330   -1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9969    1.3586   -2.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573   -0.3084   -1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5015   -2.4931    0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332   -2.4366   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6754   -3.2074    1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3518   -3.9360   -0.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7512   -2.1543   -1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9793   -1.8617   -1.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078   -0.5797   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6434    1.9825    1.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8191    3.6776    0.2546 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  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  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  6 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 20  8  1  0
 17  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  1
 10 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 24 47  1  0
M  END

HEADER    PROTEIN                                 15-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUL-20         0                                  
HETATM    1  C   UNK     0    8666.8088666.678   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.4728665.134   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8669.4808671.298   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8661.4848665.134   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8672.1448669.758   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8661.4848662.043   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8673.4808668.988   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.8908662.960   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8670.8108668.988   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8669.4768669.758   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.1428668.988   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.1428667.448   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8669.4768666.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8670.8108667.448   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.1488665.126   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.8148664.356   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.8148662.817   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8664.1478662.046   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.8098665.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8665.4758664.357   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.4758662.816   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.8098662.047   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.1428662.816   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0    8668.1428664.357   0.000  0.00  0.00           N+0
CONECT    1   12   19                                                       
CONECT    2   24                                                            
CONECT    3   10                                                            
CONECT    4   16                                                            
CONECT    5    7    9                                                       
CONECT    6    8   17                                                       
CONECT    7    5                                                            
CONECT    8    6                                                            
CONECT    9   10   14    5                                                  
CONECT   10    9   11    3                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13    1                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   16   20                                                       
CONECT   16   15   17    4                                                  
CONECT   17   16   18    6                                                  
CONECT   18   17   21                                                       
CONECT   19   20   24    1                                                  
CONECT   20   19   21   15                                                  
CONECT   21   20   22   18                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   19   23    2                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0003601
HETATM    1  C1  UNL     1       5.674   0.391  -2.489  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.881   1.280  -1.727  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.902   0.802  -0.839  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.676  -0.540  -0.674  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.715  -0.963   0.199  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.912  -0.107   0.968  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.943  -0.675   1.904  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.375  -1.107   1.433  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.342  -0.206   0.863  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.317   1.180   0.996  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.252   2.014   0.438  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.143   3.396   0.624  1.00  0.00           O  
HETATM   13  C11 UNL     1      -3.272   1.459  -0.292  1.00  0.00           C  
HETATM   14  O3  UNL     1      -4.219   2.273  -0.861  1.00  0.00           O  
HETATM   15  C12 UNL     1      -5.305   1.793  -1.627  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.349   0.113  -0.453  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.390  -0.715   0.122  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.599  -2.178  -0.063  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.430  -2.958   0.481  1.00  0.00           C  
HETATM   20  N1  UNL     1      -0.208  -2.194   0.415  1.00  0.00           N  
HETATM   21  C17 UNL     1      -0.065  -1.673  -0.906  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.157   1.219   0.786  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.139   1.680  -0.105  1.00  0.00           C  
HETATM   24  O4  UNL     1       3.383   3.035  -0.287  1.00  0.00           O  
HETATM   25  H1  UNL     1       6.352  -0.160  -1.805  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.017  -0.397  -2.961  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.263   0.902  -3.249  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.282  -1.236  -1.255  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.529  -2.030   0.336  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.464  -1.600   2.327  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.834  -0.054   2.832  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.879  -1.637   2.299  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.525   1.552   1.601  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.411   3.821   1.149  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.764   0.946  -1.039  1.00  0.00           H  
HETATM   36  H12 UNL     1      -6.104   2.533  -1.743  1.00  0.00           H  
HETATM   37  H13 UNL     1      -4.997   1.359  -2.594  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.157  -0.308  -1.028  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.501  -2.493   0.520  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.833  -2.437  -1.125  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.675  -3.207   1.554  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.352  -3.936  -0.031  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.751  -2.154  -1.490  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.979  -1.862  -1.510  1.00  0.00           H  
HETATM   45  H21 UNL     1       0.108  -0.580  -0.962  1.00  0.00           H  
HETATM   46  H22 UNL     1       1.643   1.983   1.312  1.00  0.00           H  
HETATM   47  H23 UNL     1       2.819   3.678   0.255  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   22
CONECT    7    8   30   31
CONECT    8    9   20   32
CONECT    9   10   10   17
CONECT   10   11   33
CONECT   11   12   13   13
CONECT   12   34
CONECT   13   14   16
CONECT   14   15
CONECT   15   35   36   37
CONECT   16   17   17   38
CONECT   17   18
CONECT   18   19   39   40
CONECT   19   20   41   42
CONECT   20   21
CONECT   21   43   44   45
CONECT   22   23   23   46
CONECT   23   24
CONECT   24   47
END

HMDB0003601
     RDKit          3D
(S)-Reticuline
 47 49  0  0  0  0  0  0  0  0999 V2000
    5.6741    0.3907   -2.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8805    1.2798   -1.7268 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019    0.8021   -0.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6759   -0.5403   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7152   -0.9632    0.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121   -0.1070    0.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433   -0.6752    1.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750   -1.1068    1.4335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3419   -0.2063    0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3166    1.1798    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2517    2.0143    0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1426    3.3961    0.6243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2723    1.4591   -0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2193    2.2734   -0.8606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3048    1.7933   -1.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3492    0.1127   -0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903   -0.7145    0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5989   -2.1782   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296   -2.9578    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -2.1945    0.4152 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0651   -1.6731   -0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570    1.2190    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1387    1.6803   -0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3830    3.0350   -0.2870 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3518   -0.1604   -1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170   -0.3969   -2.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2632    0.9021   -3.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2817   -1.2360   -1.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -2.0301    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4642   -1.5997    2.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8342   -0.0535    2.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8794   -1.6365    2.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5248    1.5516    1.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111    3.8206    1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7642    0.9456   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1043    2.5330   -1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9969    1.3586   -2.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573   -0.3084   -1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5015   -2.4931    0.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8332   -2.4366   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6754   -3.2074    1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3518   -3.9360   -0.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7512   -2.1543   -1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9793   -1.8617   -1.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078   -0.5797   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6434    1.9825    1.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8191    3.6776    0.2546 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  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  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  6 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 20  8  1  0
 17  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  1
 10 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 24 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Reticuline	ChEBI
(S)-(+)-Reticuline	ChEBI
L-(+)-Reticuline	ChEBI
Reticline	ChEBI
Reticulin	HMDB
Reticuline	HMDB
S-(+)-Reticuline	HMDB
(1S)-1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol	HMDB
(S)-Reticulene	HMDB
(S)-Reticuline	HMDB

Chemical Formula

C₁₉H₂₃NO₄

Average Molecular Weight

329.3902

Monoisotopic Molecular Weight

329.162708229

IUPAC Name

(1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

Traditional Name

(+,-)-reticuline

CAS Registry Number

485-19-8

SMILES

COC1=C(O)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(O)C=C23)C=C1

InChI Identifier

InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1

InChI Key

BHLYRWXGMIUIHG-HNNXBMFYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Methoxyphenol
Tetrahydroisoquinoline
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

reticuline (CHEBI:16718 )
Isoquinoline alkaloids (C02105 )

Ontology

Not Available

Physical Properties

State

Solid

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
Water Solubility	0.17 g/L	ALOGPS
logP	2.71	ALOGPS
logP	3.1	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	7.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.84 m³·mol⁻¹	ChemAxon
Polarizability	36.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	176.377	31661259
DarkChem	[M-H]-	178.312	31661259
DeepCCS	[M-2H]-	218.628	30932474
DeepCCS	[M+Na]+	193.856	30932474
AllCCS	[M+H]+	181.1	32859911
AllCCS	[M+H-H2O]+	177.9	32859911
AllCCS	[M+NH4]+	184.1	32859911
AllCCS	[M+Na]+	185.0	32859911
AllCCS	[M-H]-	184.8	32859911
AllCCS	[M+Na-2H]-	184.9	32859911
AllCCS	[M+HCOO]-	185.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-Reticuline	COC1=C(O)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(O)C=C23)C=C1	4346.7	Standard polar	33892256
(S)-Reticuline	COC1=C(O)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(O)C=C23)C=C1	2766.7	Standard non polar	33892256
(S)-Reticuline	COC1=C(O)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(O)C=C23)C=C1	2817.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-Reticuline,1TMS,isomer #1	COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(OC)C(O[Si](C)(C)C)=C1)N(C)CC2	2743.3	Semi standard non polar	33892256
(S)-Reticuline,1TMS,isomer #2	COC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C)=C(OC)C=C3CCN2C)C=C1O	2735.7	Semi standard non polar	33892256
(S)-Reticuline,2TMS,isomer #1	COC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C)=C(OC)C=C3CCN2C)C=C1O[Si](C)(C)C	2720.9	Semi standard non polar	33892256
(S)-Reticuline,1TBDMS,isomer #1	COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C1)N(C)CC2	2980.3	Semi standard non polar	33892256
(S)-Reticuline,1TBDMS,isomer #2	COC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C(C)(C)C)=C(OC)C=C3CCN2C)C=C1O	2973.1	Semi standard non polar	33892256
(S)-Reticuline,2TBDMS,isomer #1	COC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C(C)(C)C)=C(OC)C=C3CCN2C)C=C1O[Si](C)(C)C(C)(C)C	3152.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Reticuline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0900000000-480c5be967ad0cdfe3a1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Reticuline GC-MS (2 TMS) - 70eV, Positive	splash10-08fr-1290200000-e4ec7775ca969ba4d67d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Reticuline 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 - (S)-Reticuline 10V, Positive-QTOF	splash10-001i-0009000000-efd80efd0b57900a92da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Reticuline 20V, Positive-QTOF	splash10-0f7p-0934000000-7c33a1bd7de9666c1d8f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Reticuline 40V, Positive-QTOF	splash10-0fk9-1920000000-12f84a978a4144057a4d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Reticuline 10V, Negative-QTOF	splash10-004i-0009000000-4d4cbd0c33fe742e473f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Reticuline 20V, Negative-QTOF	splash10-004i-0029000000-2bde34377f488f00c9fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Reticuline 40V, Negative-QTOF	splash10-06zc-0191000000-c4dcb047f808604a6e88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Reticuline 10V, Positive-QTOF	splash10-001i-0019000000-e3b1ce90ac36f283f151	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Reticuline 20V, Positive-QTOF	splash10-000x-0932000000-ab4976b621ab97468da0	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Reticuline 40V, Positive-QTOF	splash10-0imj-0921000000-bc3bc4c37bf770f60e62	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Reticuline 10V, Negative-QTOF	splash10-004i-0009000000-48c9693a0346ebfa2d97	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Reticuline 20V, Negative-QTOF	splash10-004i-0169000000-ecf1a66856c22584f73c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Reticuline 40V, Negative-QTOF	splash10-00wa-0492000000-ef65d9cac11130e20cb8	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Epithelial ovarian cancer	23163809	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6967

PubChem Compound

439653

PDB ID

Not Available

ChEBI ID

16718

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Vanderlaan, Douglas G.; Schwartz, Martin A. Synthesis and oxidative coupling of (±)-3-oxoreticuline. Journal of Organic Chemistry (1985), 50(6), 743-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

Al-Amri AM, Smith RM, El-Haj BM, Juma'a MH: The GC-MS detection and characterization of reticuline as a marker of opium use. Forensic Sci Int. 2004 Mar 10;140(2-3):175-83. [PubMed:15036439 ]
Al-Amri AM, Smith RM, El-Haj BM, Juma'a MH: The GC-MS detection and characterization of reticuline as a marker of opium use. Forensic Sci Int. 2004 May 28;142(1):61-9. [PubMed:15272474 ]
Poeaknapo C, Schmidt J, Brandsch M, Drager B, Zenk MH: Endogenous formation of morphine in human cells. Proc Natl Acad Sci U S A. 2004 Sep 28;101(39):14091-6. Epub 2004 Sep 21. [PubMed:15383669 ]
Poeaknapo C: Mammalian morphine: de novo formation of morphine in human cells. Med Sci Monit. 2005 May;11(5):MS6-17. Epub 2005 Apr 28. [PubMed:15874902 ]
Boettcher C, Fellermeier M, Boettcher C, Drager B, Zenk MH: How human neuroblastoma cells make morphine. Proc Natl Acad Sci U S A. 2005 Jun 14;102(24):8495-500. Epub 2005 Jun 3. [PubMed:15937106 ]

Showing metabocard for (S)-Reticuline (HMDB0003601)

MOL for HMDB0003601 ((S)-Reticuline)

3D MOL for HMDB0003601 ((S)-Reticuline)

3D SDF for HMDB0003601 ((S)-Reticuline)

3D-SDF for HMDB0003601 ((S)-Reticuline)

PDB for HMDB0003601 ((S)-Reticuline)

3D PDB for HMDB0003601 ((S)-Reticuline)

SMILES for HMDB0003601 ((S)-Reticuline)

INCHI for HMDB0003601 ((S)-Reticuline)

Structure for HMDB0003601 ((S)-Reticuline)

3D Structure for HMDB0003601 ((S)-Reticuline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra