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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-28 21:29:43 UTC

Update Date

2021-09-26 22:48:54 UTC

HMDB ID

HMDB0242264

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-Thaliporphine

Description

(+)-Thaliporphine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Based on a literature review a significant number of articles have been published on (+)-Thaliporphine. This compound has been identified in human blood as reported by (PMID: 31557052 ). (+)-thaliporphine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (+)-Thaliporphine 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


  Mrv1533004261516522D          

 25 28  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
  5 25  2  0  0  0  0
 10 25  1  0  0  0  0
M  END

HMDB0242264
     RDKit          3D
(+)-Thaliporphine
 48 51  0  0  0  0  0  0  0  0999 V2000
    5.5286   -1.2476   -1.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912   -0.2398   -0.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7181   -0.0618   -0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222   -0.8695   -1.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4671   -0.6877   -0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0399    0.3034    0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9459    1.0983    0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128    0.9101    0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2777    1.7179    1.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7856    2.6986    2.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3912    0.4067    0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8354    1.4650    1.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    2.4065    1.8123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1939    1.6140    1.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7054    2.6656    2.1690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0554    2.8839    2.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0841    0.7213    0.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6307   -0.3480    0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2713   -0.5117   -0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375   -1.7046   -0.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4716   -1.4741   -1.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313   -2.4964   -1.4494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9765   -2.0506   -2.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9204   -2.6223   -0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6087   -1.3069   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9425   -1.2010   -2.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5897   -1.0947   -1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3632   -2.2538   -1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1078   -1.6573   -1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6854    1.8559    1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0539    3.3752    1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715    3.2429    2.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    2.1511    2.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183    3.1828    2.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5722    3.4492    1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6480    1.9738    2.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1378    3.5048    3.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563    0.8041    1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -2.4010    0.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2911   -1.0006   -2.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700   -2.4805   -1.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1210   -2.3847   -3.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1682   -0.9687   -2.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8720   -2.5716   -3.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5649   -3.4036   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5807   -2.9668    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187   -0.9515   -1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4704   -1.4744    0.2347 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
  6 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  8  3  1  0
 19 11  1  0
 21  5  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 25 48  1  0
M  END


  Mrv1533004261516522D          

 25 28  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
  5 25  2  0  0  0  0
 10 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242264

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C3C(CC4=CC(OC)=C(OC)C=C4C3=C1O)N(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO4/c1-21-6-5-11-8-17(25-4)20(22)19-13-10-16(24-3)15(23-2)9-12(13)7-14(21)18(11)19/h8-10,14,22H,5-7H2,1-4H3

> <INCHI_KEY>
SAERKXUSZPTMCQ-UHFFFAOYSA-N

> <FORMULA>
C20H23NO4

> <MOLECULAR_WEIGHT>
341.407

> <EXACT_MASS>
341.162708225

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.88232646045023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5,15-trimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,13(17),14-hexaen-16-ol

> <ALOGPS_LOGP>
2.87

> <JCHEM_LOGP>
2.924832909

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.922206131418967

> <JCHEM_PKA_STRONGEST_BASIC>
6.570596709208694

> <JCHEM_POLAR_SURFACE_AREA>
51.160000000000004

> <JCHEM_REFRACTIVITY>
97.39679999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,15-trimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,13(17),14-hexaen-16-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242264
     RDKit          3D
(+)-Thaliporphine
 48 51  0  0  0  0  0  0  0  0999 V2000
    5.5286   -1.2476   -1.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912   -0.2398   -0.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7181   -0.0618   -0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222   -0.8695   -1.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4671   -0.6877   -0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0399    0.3034    0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9459    1.0983    0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128    0.9101    0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2777    1.7179    1.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7856    2.6986    2.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3912    0.4067    0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8354    1.4650    1.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    2.4065    1.8123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1939    1.6140    1.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7054    2.6656    2.1690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0554    2.8839    2.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0841    0.7213    0.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6307   -0.3480    0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2713   -0.5117   -0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375   -1.7046   -0.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4716   -1.4741   -1.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313   -2.4964   -1.4494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9765   -2.0506   -2.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9204   -2.6223   -0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6087   -1.3069   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9425   -1.2010   -2.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5897   -1.0947   -1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3632   -2.2538   -1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1078   -1.6573   -1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6854    1.8559    1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0539    3.3752    1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715    3.2429    2.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    2.1511    2.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183    3.1828    2.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5722    3.4492    1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6480    1.9738    2.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1378    3.5048    3.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563    0.8041    1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -2.4010    0.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2911   -1.0006   -2.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700   -2.4805   -1.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1210   -2.3847   -3.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1682   -0.9687   -2.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8720   -2.5716   -3.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5649   -3.4036   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5807   -2.9668    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187   -0.9515   -1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4704   -1.4744    0.2347 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
  6 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  8  3  1  0
 19 11  1  0
 21  5  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 25 48  1  0
M  END

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.667  -0.000   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   25                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   12   22                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22    3   24                                                  
CONECT   24   23                                                            
CONECT   25   22    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0242264
HETATM    1  C1  UNL     1       5.529  -1.248  -1.529  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.091  -0.240  -0.619  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.718  -0.062  -0.373  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.822  -0.869  -1.018  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.467  -0.688  -0.770  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.040   0.303   0.127  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.946   1.098   0.759  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.313   0.910   0.502  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.278   1.718   1.140  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.786   2.699   2.028  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.391   0.407   0.485  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.835   1.465   1.231  1.00  0.00           C  
HETATM   13  O3  UNL     1      -0.043   2.406   1.812  1.00  0.00           O  
HETATM   14  C11 UNL     1      -2.194   1.614   1.423  1.00  0.00           C  
HETATM   15  O4  UNL     1      -2.705   2.666   2.169  1.00  0.00           O  
HETATM   16  C12 UNL     1      -4.055   2.884   2.408  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.084   0.721   0.878  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.631  -0.348   0.127  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.271  -0.512  -0.072  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.737  -1.705  -0.747  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.472  -1.474  -1.534  1.00  0.00           C  
HETATM   22  N1  UNL     1      -1.731  -2.496  -1.449  1.00  0.00           N  
HETATM   23  C18 UNL     1      -1.977  -2.051  -2.777  1.00  0.00           C  
HETATM   24  C19 UNL     1      -2.920  -2.622  -0.635  1.00  0.00           C  
HETATM   25  C20 UNL     1      -3.609  -1.307  -0.458  1.00  0.00           C  
HETATM   26  H1  UNL     1       4.943  -1.201  -2.480  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.590  -1.095  -1.800  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.363  -2.254  -1.096  1.00  0.00           H  
HETATM   29  H4  UNL     1       3.108  -1.657  -1.723  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.685   1.856   1.449  1.00  0.00           H  
HETATM   31  H6  UNL     1       3.054   3.375   1.526  1.00  0.00           H  
HETATM   32  H7  UNL     1       4.571   3.243   2.552  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.203   2.151   2.826  1.00  0.00           H  
HETATM   34  H9  UNL     1      -0.318   3.183   2.356  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.572   3.449   1.619  1.00  0.00           H  
HETATM   36  H11 UNL     1      -4.648   1.974   2.607  1.00  0.00           H  
HETATM   37  H12 UNL     1      -4.138   3.505   3.341  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.156   0.804   1.004  1.00  0.00           H  
HETATM   39  H14 UNL     1      -0.425  -2.401   0.116  1.00  0.00           H  
HETATM   40  H15 UNL     1       0.291  -1.001  -2.529  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.970  -2.480  -1.698  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.121  -2.385  -3.428  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.168  -0.969  -2.883  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.872  -2.572  -3.163  1.00  0.00           H  
HETATM   45  H20 UNL     1      -3.565  -3.404  -1.056  1.00  0.00           H  
HETATM   46  H21 UNL     1      -2.581  -2.967   0.371  1.00  0.00           H  
HETATM   47  H22 UNL     1      -4.019  -0.952  -1.419  1.00  0.00           H  
HETATM   48  H23 UNL     1      -4.470  -1.474   0.235  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   29
CONECT    5    6    6   21
CONECT    6    7   11
CONECT    7    8    8   30
CONECT    8    9
CONECT    9   10
CONECT   10   31   32   33
CONECT   11   12   12   19
CONECT   12   13   14
CONECT   13   34
CONECT   14   15   17   17
CONECT   15   16
CONECT   16   35   36   37
CONECT   17   18   38
CONECT   18   19   19   25
CONECT   19   20
CONECT   20   21   22   39
CONECT   21   40   41
CONECT   22   23   24
CONECT   23   42   43   44
CONECT   24   25   45   46
CONECT   25   47   48
END

HMDB0242264
     RDKit          3D
(+)-Thaliporphine
 48 51  0  0  0  0  0  0  0  0999 V2000
    5.5286   -1.2476   -1.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912   -0.2398   -0.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7181   -0.0618   -0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222   -0.8695   -1.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4671   -0.6877   -0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0399    0.3034    0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9459    1.0983    0.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128    0.9101    0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2777    1.7179    1.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7856    2.6986    2.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3912    0.4067    0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8354    1.4650    1.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    2.4065    1.8123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1939    1.6140    1.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7054    2.6656    2.1690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0554    2.8839    2.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0841    0.7213    0.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6307   -0.3480    0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2713   -0.5117   -0.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375   -1.7046   -0.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4716   -1.4741   -1.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313   -2.4964   -1.4494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9765   -2.0506   -2.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9204   -2.6223   -0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6087   -1.3069   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9425   -1.2010   -2.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5897   -1.0947   -1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3632   -2.2538   -1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1078   -1.6573   -1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6854    1.8559    1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0539    3.3752    1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715    3.2429    2.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    2.1511    2.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183    3.1828    2.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5722    3.4492    1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6480    1.9738    2.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1378    3.5048    3.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563    0.8041    1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -2.4010    0.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2911   -1.0006   -2.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700   -2.4805   -1.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1210   -2.3847   -3.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1682   -0.9687   -2.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8720   -2.5716   -3.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5649   -3.4036   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5807   -2.9668    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0187   -0.9515   -1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4704   -1.4744    0.2347 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
  6 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
  8  3  1  0
 19 11  1  0
 21  5  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 25 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Thaliporphine hydrochloride	HMDB

Chemical Formula

C₂₀H₂₃NO₄

Average Molecular Weight

341.407

Monoisotopic Molecular Weight

341.162708225

IUPAC Name

4,5,15-trimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,13(17),14-hexaen-16-ol

Traditional Name

4,5,15-trimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,13(17),14-hexaen-16-ol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3C(CC4=CC(OC)=C(OC)C=C4C3=C1O)N(C)CC2

InChI Identifier

InChI=1S/C20H23NO4/c1-21-6-5-11-8-17(25-4)20(22)19-13-10-16(24-3)15(23-2)9-12(13)7-14(21)18(11)19/h8-10,14,22H,5-7H2,1-4H3

InChI Key

SAERKXUSZPTMCQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
1-naphthol
Naphthalene
Quinoline
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Ether
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.87	ALOGPS
logP	2.92	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.92	ChemAxon
pKa (Strongest Basic)	6.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.16 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.4 m³·mol⁻¹	ChemAxon
Polarizability	37.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	186.957	30932474
DeepCCS	[M-H]-	184.599	30932474
DeepCCS	[M-2H]-	218.89	30932474
DeepCCS	[M+Na]+	194.123	30932474
AllCCS	[M+H]+	183.1	32859911
AllCCS	[M+H-H2O]+	180.3	32859911
AllCCS	[M+NH4]+	185.7	32859911
AllCCS	[M+Na]+	186.4	32859911
AllCCS	[M-H]-	184.6	32859911
AllCCS	[M+Na-2H]-	184.2	32859911
AllCCS	[M+HCOO]-	183.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.2537 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.91 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1083.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	202.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	152.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	74.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	348.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	357.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	517.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	743.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	286.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1082.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	251.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	473.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	411.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-Thaliporphine	COC1=CC2=C3C(CC4=CC(OC)=C(OC)C=C4C3=C1O)N(C)CC2	4268.2	Standard polar	33892256
(+)-Thaliporphine	COC1=CC2=C3C(CC4=CC(OC)=C(OC)C=C4C3=C1O)N(C)CC2	2828.3	Standard non polar	33892256
(+)-Thaliporphine	COC1=CC2=C3C(CC4=CC(OC)=C(OC)C=C4C3=C1O)N(C)CC2	3075.0	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

90376

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100020

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 (+)-Thaliporphine (HMDB0242264)

MOL for HMDB0242264 ((+)-Thaliporphine)

3D MOL for HMDB0242264 ((+)-Thaliporphine)

3D SDF for HMDB0242264 ((+)-Thaliporphine)

3D-SDF for HMDB0242264 ((+)-Thaliporphine)

PDB for HMDB0242264 ((+)-Thaliporphine)

3D PDB for HMDB0242264 ((+)-Thaliporphine)

SMILES for HMDB0242264 ((+)-Thaliporphine)

INCHI for HMDB0242264 ((+)-Thaliporphine)

Structure for HMDB0242264 ((+)-Thaliporphine)

3D Structure for HMDB0242264 ((+)-Thaliporphine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized