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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:03:10 UTC

Update Date

2019-07-23 07:15:13 UTC

HMDB ID

HMDB0060846

Secondary Accession Numbers

HMDB60846

Metabolite Identification

Common Name

N-Monodemethylolopatadine

Description

N-Monodemethylolopatadine is a metabolite of olopatadine. Olopatadine hydrochloride is an antihistamine (as well as anticholinergic) and mast cell stabilizer, sold as a prescription eye drop (0.2% solution, Pataday, manufactured by Alcon). It is used to treat itching associated with allergic conjunctivitis. Olopatadine hydrochloride 0.1% is sold as Patanol (or Opatanol in some countries). A nasal spray formulation is sold as Patanase, which was approved by the FDA on April 15, 2008. (Wikipedia)

Structure

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

HMDB0060846
     RDKit          3D
N-Monodemethylolopatadine
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.8814   -1.3148   -0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6921   -0.8801    0.7218 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552   -1.4724    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2929   -1.0747    0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -1.5587    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9939   -0.7963   -0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432   -1.4368   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9087   -2.4574   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9874   -3.1614   -1.8943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2844   -2.7942   -1.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5613   -1.7470   -0.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4984   -1.0110   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9982    0.0479    0.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1003    0.9052    1.3552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8248    1.3732    0.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5249    2.6572    1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2825    3.1861    0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566    2.3837    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9642    2.9452   -0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8976    3.5355   -1.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8284    3.5030   -2.1709 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0100    4.1095   -2.0861 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3734    1.0639   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8533    0.6338    0.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -1.5796   -1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3123   -2.2069    0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6735   -0.5389   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6921   -1.2068    1.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -2.5758    0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271   -1.2131   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260   -1.7971    1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3104   -0.2493    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -2.6192    0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8758   -2.6732   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7928   -3.9758   -2.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1252   -3.3372   -1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5583   -1.4782   -0.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6790    0.6907    0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6122   -0.4201    1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2595    3.2648    1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0837    4.2188    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758    3.7205    0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7068    2.0958   -0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414    4.7553   -1.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334    0.4858   -0.6720 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
  9 10  2  0
 10 11  1  0
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 13 14  1  0
 14 15  1  0
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 18 19  1  0
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 23 24  2  0
 24  6  1  0
 12  7  1  0
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  9 35  1  0
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 11 37  1  0
 13 38  1  0
 13 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 22 44  1  0
 23 45  1  0
M  END


  Mrv0541 07041312032D          

 24 26  0  0  0  0            999 V2000
    2.3747    3.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    2.8070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0892    2.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0892    1.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    1.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    0.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -1.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -1.4753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -0.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625    0.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2741    0.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906   -0.1944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3306    1.1711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189   -1.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237   -0.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401    0.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517    0.5352    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  1  0  0  0  0
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  5  6  2  0  0  0  0
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  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  7 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060846

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCC\C=C1\C2=C(COC3=C1C=C(CC(O)=O)C=C3)C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H21NO3/c1-21-10-4-7-17-16-6-3-2-5-15(16)13-24-19-9-8-14(11-18(17)19)12-20(22)23/h2-3,5-9,11,21H,4,10,12-13H2,1H3,(H,22,23)/b17-7-

> <INCHI_KEY>
VQMJUHOJPCPUAM-IDUWFGFVSA-N

> <FORMULA>
C20H21NO3

> <MOLECULAR_WEIGHT>
323.3856

> <EXACT_MASS>
323.152143543

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.722856054407785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2Z)-2-[3-(methylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]acetic acid

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
0.6228587032456545

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.784032152814179

> <JCHEM_PKA_STRONGEST_BASIC>
10.471608588559839

> <JCHEM_POLAR_SURFACE_AREA>
58.559999999999995

> <JCHEM_REFRACTIVITY>
104.25770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2Z)-2-[3-(methylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060846
     RDKit          3D
N-Monodemethylolopatadine
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.8814   -1.3148   -0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6921   -0.8801    0.7218 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552   -1.4724    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2929   -1.0747    0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -1.5587    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9939   -0.7963   -0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432   -1.4368   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9087   -2.4574   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9874   -3.1614   -1.8943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2844   -2.7942   -1.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5613   -1.7470   -0.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4984   -1.0110   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9982    0.0479    0.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1003    0.9052    1.3552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8248    1.3732    0.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5249    2.6572    1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2825    3.1861    0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566    2.3837    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9642    2.9452   -0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8976    3.5355   -1.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8284    3.5030   -2.1709 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0100    4.1095   -2.0861 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3734    1.0639   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8533    0.6338    0.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -1.5796   -1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3123   -2.2069    0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6735   -0.5389   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6921   -1.2068    1.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -2.5758    0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271   -1.2131   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260   -1.7971    1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3104   -0.2493    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -2.6192    0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8758   -2.6732   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7928   -3.9758   -2.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1252   -3.3372   -1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5583   -1.4782   -0.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6790    0.6907    0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6122   -0.4201    1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2595    3.2648    1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0837    4.2188    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758    3.7205    0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7068    2.0958   -0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414    4.7553   -1.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334    0.4858   -0.6720 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
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  1  0
 23 24  2  0
 24  6  1  0
 12  7  1  0
 24 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 22 44  1  0
 23 45  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       4.433   6.780   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.433   5.240   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.767   4.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.767   2.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.100   2.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.100   0.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.488  -0.049   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.830  -1.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.870  -2.754   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.330  -2.754   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.370  -1.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.713  -0.049   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.584   0.999   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.112   0.545   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.983   1.592   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.512   1.139   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.169  -0.363   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.617   2.186   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.770  -0.956   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.898  -2.004   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.302  -2.004   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.431  -0.956   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.088   0.545   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.617   0.999   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20                                                       
CONECT   20   19   11                                                       
CONECT   21    8   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    7                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0060846
HETATM    1  C1  UNL     1       4.881  -1.315  -0.008  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.692  -0.880   0.722  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.555  -1.472   0.045  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.293  -1.075   0.733  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.025  -1.559   0.219  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.994  -0.796  -0.006  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.243  -1.437  -0.526  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.909  -2.457  -1.360  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.987  -3.161  -1.894  1.00  0.00           C  
HETATM   10  C9  UNL     1      -4.284  -2.794  -1.559  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.561  -1.747  -0.706  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.498  -1.011  -0.145  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.998   0.048   0.726  1.00  0.00           C  
HETATM   14  O1  UNL     1      -3.100   0.905   1.355  1.00  0.00           O  
HETATM   15  C13 UNL     1      -1.825   1.373   0.962  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.525   2.657   1.241  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.282   3.186   0.870  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.657   2.384   0.203  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.964   2.945  -0.186  1.00  0.00           C  
HETATM   20  C18 UNL     1       1.898   3.536  -1.541  1.00  0.00           C  
HETATM   21  O2  UNL     1       0.828   3.503  -2.171  1.00  0.00           O  
HETATM   22  O3  UNL     1       3.010   4.110  -2.086  1.00  0.00           O  
HETATM   23  C19 UNL     1       0.373   1.064  -0.096  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.853   0.634   0.306  1.00  0.00           C  
HETATM   25  H1  UNL     1       4.604  -1.580  -1.062  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.312  -2.207   0.497  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.673  -0.539  -0.010  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.692  -1.207   1.694  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.750  -2.576   0.047  1.00  0.00           H  
HETATM   30  H6  UNL     1       2.627  -1.213  -1.030  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.426  -1.797   1.654  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.310  -0.249   1.458  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.082  -2.619   0.019  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.876  -2.673  -1.588  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.793  -3.976  -2.556  1.00  0.00           H  
HETATM   36  H12 UNL     1      -5.125  -3.337  -1.970  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.558  -1.478  -0.459  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.679   0.691   0.091  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.612  -0.420   1.528  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.260   3.265   1.755  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.084   4.219   1.116  1.00  0.00           H  
HETATM   42  H18 UNL     1       2.276   3.720   0.558  1.00  0.00           H  
HETATM   43  H19 UNL     1       2.707   2.096  -0.148  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.541   4.755  -1.509  1.00  0.00           H  
HETATM   45  H21 UNL     1       1.033   0.486  -0.672  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6    6   33
CONECT    6    7   24
CONECT    7    8    8   12
CONECT    8    9   34
CONECT    9   10   10   35
CONECT   10   11   36
CONECT   11   12   12   37
CONECT   12   13
CONECT   13   14   38   39
CONECT   14   15
CONECT   15   16   16   24
CONECT   16   17   40
CONECT   17   18   18   41
CONECT   18   19   23
CONECT   19   20   42   43
CONECT   20   21   21   22
CONECT   22   44
CONECT   23   24   24   45
END

HMDB0060846
     RDKit          3D
N-Monodemethylolopatadine
 45 47  0  0  0  0  0  0  0  0999 V2000
    4.8814   -1.3148   -0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6921   -0.8801    0.7218 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552   -1.4724    0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2929   -1.0747    0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0250   -1.5587    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9939   -0.7963   -0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432   -1.4368   -0.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9087   -2.4574   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9874   -3.1614   -1.8943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2844   -2.7942   -1.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5613   -1.7470   -0.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4984   -1.0110   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9982    0.0479    0.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1003    0.9052    1.3552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8248    1.3732    0.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5249    2.6572    1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2825    3.1861    0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566    2.3837    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9642    2.9452   -0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8976    3.5355   -1.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8284    3.5030   -2.1709 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0100    4.1095   -2.0861 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3734    1.0639   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8533    0.6338    0.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -1.5796   -1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3123   -2.2069    0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6735   -0.5389   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6921   -1.2068    1.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -2.5758    0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271   -1.2131   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260   -1.7971    1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3104   -0.2493    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -2.6192    0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8758   -2.6732   -1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7928   -3.9758   -2.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1252   -3.3372   -1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5583   -1.4782   -0.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6790    0.6907    0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6122   -0.4201    1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2595    3.2648    1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0837    4.2188    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758    3.7205    0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7068    2.0958   -0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414    4.7553   -1.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334    0.4858   -0.6720 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
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  1  0
 23 24  2  0
 24  6  1  0
 12  7  1  0
 24 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 22 44  1  0
 23 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₁NO₃

Average Molecular Weight

323.3856

Monoisotopic Molecular Weight

323.152143543

IUPAC Name

2-[(2Z)-2-[3-(methylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]acetic acid

Traditional Name

[(2Z)-2-[3-(methylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]acetic acid

CAS Registry Number

Not Available

SMILES

CNCC\C=C1\C2=C(COC3=C1C=C(CC(O)=O)C=C3)C=CC=C2

InChI Identifier

InChI=1S/C20H21NO3/c1-21-10-4-7-17-16-6-3-2-5-15(16)13-24-19-9-8-14(11-18(17)19)12-20(22)23/h2-3,5-9,11,21H,4,10,12-13H2,1H3,(H,22,23)/b17-7-

InChI Key

VQMJUHOJPCPUAM-IDUWFGFVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxepines

Sub Class

Dibenzoxepines

Direct Parent

Dibenzoxepines

Alternative Parents

Substituents

Dibenzoxepine
Alkyl aryl ether
Benzenoid
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Oxacycle
Secondary amine
Ether
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060846)
Liver (HMDB: HMDB0060846)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060846)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060846)

Cellular substructure

Cytoplasm (HMDB: HMDB0060846)

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
Water Solubility	0.0038 g/L	ALOGPS
logP	1.5	ALOGPS
logP	0.62	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	10.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.26 m³·mol⁻¹	ChemAxon
Polarizability	35.72 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]+	181.798	31661259
DarkChem	[M-H]-	179.637	31661259
DeepCCS	[M+H]+	184.493	30932474
DeepCCS	[M-H]-	182.135	30932474
DeepCCS	[M-2H]-	216.162	30932474
DeepCCS	[M+Na]+	191.766	30932474
AllCCS	[M+H]+	177.9	32859911
AllCCS	[M+H-H2O]+	174.7	32859911
AllCCS	[M+NH4]+	180.9	32859911
AllCCS	[M+Na]+	181.7	32859911
AllCCS	[M-H]-	182.6	32859911
AllCCS	[M+Na-2H]-	182.5	32859911
AllCCS	[M+HCOO]-	182.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Monodemethylolopatadine	CNCC\C=C1\C2=C(COC3=C1C=C(CC(O)=O)C=C3)C=CC=C2	4265.5	Standard polar	33892256
N-Monodemethylolopatadine	CNCC\C=C1\C2=C(COC3=C1C=C(CC(O)=O)C=C3)C=CC=C2	2811.1	Standard non polar	33892256
N-Monodemethylolopatadine	CNCC\C=C1\C2=C(COC3=C1C=C(CC(O)=O)C=C3)C=CC=C2	2766.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Monodemethylolopatadine,1TMS,isomer #1	CNCC/C=C1/C2=CC=CC=C2COC2=CC=C(CC(=O)O[Si](C)(C)C)C=C12	2889.0	Semi standard non polar	33892256
N-Monodemethylolopatadine,1TMS,isomer #2	CN(CC/C=C1/C2=CC=CC=C2COC2=CC=C(CC(=O)O)C=C12)[Si](C)(C)C	3080.3	Semi standard non polar	33892256
N-Monodemethylolopatadine,2TMS,isomer #1	CN(CC/C=C1/C2=CC=CC=C2COC2=CC=C(CC(=O)O[Si](C)(C)C)C=C12)[Si](C)(C)C	3013.6	Semi standard non polar	33892256
N-Monodemethylolopatadine,2TMS,isomer #1	CN(CC/C=C1/C2=CC=CC=C2COC2=CC=C(CC(=O)O[Si](C)(C)C)C=C12)[Si](C)(C)C	2941.9	Standard non polar	33892256
N-Monodemethylolopatadine,2TMS,isomer #1	CN(CC/C=C1/C2=CC=CC=C2COC2=CC=C(CC(=O)O[Si](C)(C)C)C=C12)[Si](C)(C)C	3557.4	Standard polar	33892256
N-Monodemethylolopatadine,1TBDMS,isomer #1	CNCC/C=C1/C2=CC=CC=C2COC2=CC=C(CC(=O)O[Si](C)(C)C(C)(C)C)C=C12	3142.1	Semi standard non polar	33892256
N-Monodemethylolopatadine,1TBDMS,isomer #2	CN(CC/C=C1/C2=CC=CC=C2COC2=CC=C(CC(=O)O)C=C12)[Si](C)(C)C(C)(C)C	3278.6	Semi standard non polar	33892256
N-Monodemethylolopatadine,2TBDMS,isomer #1	CN(CC/C=C1/C2=CC=CC=C2COC2=CC=C(CC(=O)O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	3482.8	Semi standard non polar	33892256
N-Monodemethylolopatadine,2TBDMS,isomer #1	CN(CC/C=C1/C2=CC=CC=C2COC2=CC=C(CC(=O)O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	3400.5	Standard non polar	33892256
N-Monodemethylolopatadine,2TBDMS,isomer #1	CN(CC/C=C1/C2=CC=CC=C2COC2=CC=C(CC(=O)O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	3680.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Monodemethylolopatadine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9051000000-0d304c62938d3b676b83	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Monodemethylolopatadine GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9022000000-e35c5a0b7fa921399607	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Monodemethylolopatadine 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 - N-Monodemethylolopatadine 10V, Positive-QTOF	splash10-0a4i-0069000000-7a5feee64dd9d988da93	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodemethylolopatadine 20V, Positive-QTOF	splash10-004j-1091000000-4e757eb02e96c70394c3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodemethylolopatadine 40V, Positive-QTOF	splash10-05am-5190000000-74f8c2b58c62c6ab1109	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodemethylolopatadine 10V, Negative-QTOF	splash10-00fr-0049000000-cbd13114c5b3e1162b55	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodemethylolopatadine 20V, Negative-QTOF	splash10-0fi0-1069000000-c5cbab49ae4df82fa753	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodemethylolopatadine 40V, Negative-QTOF	splash10-0a6s-5190000000-78f860ab2c8f65396878	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodemethylolopatadine 10V, Positive-QTOF	splash10-00di-0059000000-0bea89ef987d86afa7ed	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodemethylolopatadine 20V, Positive-QTOF	splash10-002b-0090000000-8d6558dd8a1432466228	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodemethylolopatadine 40V, Positive-QTOF	splash10-000t-0090000000-1bad49a995557e2c7aac	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodemethylolopatadine 10V, Negative-QTOF	splash10-00di-0039000000-bfe90b2f1a3e0ed38834	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodemethylolopatadine 20V, Negative-QTOF	splash10-006t-0092000000-52639a7f0a903f3fd564	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodemethylolopatadine 40V, Negative-QTOF	splash10-008a-0090000000-653dd0f45a2001e709b2	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14127209

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

Not Available

Showing metabocard for N-Monodemethylolopatadine (HMDB0060846)

MOL for HMDB0060846 (N-Monodemethylolopatadine)

3D MOL for HMDB0060846 (N-Monodemethylolopatadine)

3D SDF for HMDB0060846 (N-Monodemethylolopatadine)

3D-SDF for HMDB0060846 (N-Monodemethylolopatadine)

PDB for HMDB0060846 (N-Monodemethylolopatadine)

3D PDB for HMDB0060846 (N-Monodemethylolopatadine)

SMILES for HMDB0060846 (N-Monodemethylolopatadine)

INCHI for HMDB0060846 (N-Monodemethylolopatadine)

Structure for HMDB0060846 (N-Monodemethylolopatadine)

3D Structure for HMDB0060846 (N-Monodemethylolopatadine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra