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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:32:22 UTC

Update Date

2021-09-26 23:10:49 UTC

HMDB ID

HMDB0255726

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Norchelerythrine

Description

17,18-dimethoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaene, also known as 1,2-dimethoxy-(1,3)benzodioxolo(5,6-c)phenanthridine, belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. Based on a literature review very few articles have been published on 17,18-dimethoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaene. This compound has been identified in human blood as reported by (PMID: 31557052 ). Norchelerythrine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Norchelerythrine 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


  Mrv1533004171518432D          

 25 29  0  0  0  0            999 V2000
    1.7801   -3.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839   -2.5090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781   -2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9819   -1.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7761   -1.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666   -1.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1608   -1.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3646   -0.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1588   -0.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7493   -1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5435   -0.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1339   -1.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9572   -1.4693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2622   -2.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6275   -2.7628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9301   -2.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1359   -2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5455   -1.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7512   -2.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5475   -2.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7532   -3.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1628   -2.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3686   -2.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1648   -3.6614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3706   -3.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  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
 12 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  6 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
 24 25  1  0  0  0  0
M  END

HMDB0255726
     RDKit          3D
Norchelerythrine
 40 44  0  0  0  0  0  0  0  0999 V2000
    6.0649   -0.5893   -1.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1148    0.3553   -0.9697 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7789    0.0871   -0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285   -1.1896   -1.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9710   -1.4958   -0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024   -0.5397   -0.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5921    0.7424   -0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6786    1.6927    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217    1.4210    0.2965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0892    0.1893    0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4609   -0.0140    0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2894    1.0151    0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6500    0.8224    0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1644   -0.4312    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3245   -1.4488    0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9693   -1.2636   -0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1364   -2.2761   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7635   -2.0756   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2581   -0.8424   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5275   -0.3402    0.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8128    0.8387    1.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6965    1.6517    1.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9238    1.0756   -0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018    2.3355   -0.1323 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8682    2.7907    1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0619   -0.1067   -1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1593   -1.3658   -0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7867   -1.0728   -2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -1.9773   -1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6378   -2.5047   -1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0951    2.6834    0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8774    1.9879    0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421   -2.4303   -0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5827   -3.2382   -0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1513   -2.8778   -0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8049    0.5838    2.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7693    1.3037    1.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230    2.4460    1.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2513    2.4568    1.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477    3.9105    1.0378 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 14 20  1  0
 20 21  1  0
 21 22  1  0
  7 23  2  0
 23 24  1  0
 24 25  1  0
 23  3  1  0
 19  6  1  0
 19 10  1  0
 16 11  1  0
 22 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  8 31  1  0
 12 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
 25 38  1  0
 25 39  1  0
 25 40  1  0
M  END


  Mrv1533004171518432D          

 25 29  0  0  0  0            999 V2000
    1.7801   -3.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839   -2.5090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781   -2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9819   -1.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7761   -1.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666   -1.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1608   -1.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3646   -0.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1588   -0.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7493   -1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5435   -0.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1339   -1.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9572   -1.4693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2622   -2.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6275   -2.7628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9301   -2.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1359   -2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5455   -1.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7512   -2.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5475   -2.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7532   -3.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1628   -2.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3686   -2.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1648   -3.6614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3706   -3.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  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
 12 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  6 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
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255726

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2C(C=NC3=C2C=CC2=CC4=C(OCO4)C=C32)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H15NO4/c1-22-16-6-5-12-13-4-3-11-7-17-18(25-10-24-17)8-14(11)19(13)21-9-15(12)20(16)23-2/h3-9H,10H2,1-2H3

> <INCHI_KEY>
JGUNQXPMULKFNY-UHFFFAOYSA-N

> <FORMULA>
C20H15NO4

> <MOLECULAR_WEIGHT>
333.343

> <EXACT_MASS>
333.100107967

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
35.77899153287056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17,18-dimethoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaene

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
3.4177449209999997

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.612168156237134

> <JCHEM_POLAR_SURFACE_AREA>
49.81

> <JCHEM_REFRACTIVITY>
91.57299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
norchelerythrine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255726
     RDKit          3D
Norchelerythrine
 40 44  0  0  0  0  0  0  0  0999 V2000
    6.0649   -0.5893   -1.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1148    0.3553   -0.9697 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7789    0.0871   -0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285   -1.1896   -1.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9710   -1.4958   -0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024   -0.5397   -0.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5921    0.7424   -0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6786    1.6927    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217    1.4210    0.2965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0892    0.1893    0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4609   -0.0140    0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2894    1.0151    0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6500    0.8224    0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1644   -0.4312    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3245   -1.4488    0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9693   -1.2636   -0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1364   -2.2761   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7635   -2.0756   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2581   -0.8424   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5275   -0.3402    0.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8128    0.8387    1.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6965    1.6517    1.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9238    1.0756   -0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018    2.3355   -0.1323 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8682    2.7907    1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0619   -0.1067   -1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1593   -1.3658   -0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7867   -1.0728   -2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -1.9773   -1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6378   -2.5047   -1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0951    2.6834    0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8774    1.9879    0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421   -2.4303   -0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5827   -3.2382   -0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1513   -2.8778   -0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8049    0.5838    2.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7693    1.3037    1.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230    2.4460    1.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2513    2.4568    1.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477    3.9105    1.0378 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 14 20  1  0
 20 21  1  0
 21 22  1  0
  7 23  2  0
 23 24  1  0
 24 25  1  0
 23  3  1  0
 19  6  1  0
 19 10  1  0
 16 11  1  0
 22 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  8 31  1  0
 12 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
 25 38  1  0
 25 39  1  0
 25 40  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       3.323  -6.176   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.703  -4.683   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.186  -4.267   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.566  -2.774   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.049  -2.358   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.151  -3.433   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.633  -3.017   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.014  -1.524   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.496  -1.108   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.599  -2.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.081  -1.766   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.183  -2.842   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      16.720  -2.743   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      17.289  -4.174   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.105  -5.157   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.803  -4.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.320  -4.751   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.218  -3.675   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.736  -4.092   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      10.355  -5.584   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       8.873  -6.001   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.771  -4.926   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.288  -5.342   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.908  -6.835   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.425  -7.251   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                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   10   19                                                  
CONECT   19   18    7   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    6   23                                                  
CONECT   23   22    3   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

COMPND    HMDB0255726
HETATM    1  C1  UNL     1       6.065  -0.589  -1.392  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.115   0.355  -0.970  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.779   0.087  -0.818  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.328  -1.190  -1.094  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.971  -1.496  -0.949  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.102  -0.540  -0.537  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.592   0.742  -0.266  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.679   1.693   0.151  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.622   1.421   0.296  1.00  0.00           N  
HETATM   10  C8  UNL     1      -1.089   0.189   0.035  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.461  -0.014   0.211  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.289   1.015   0.636  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.650   0.822   0.813  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.164  -0.431   0.554  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.325  -1.449   0.131  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.969  -1.264  -0.048  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.136  -2.276  -0.469  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.764  -2.076  -0.646  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.258  -0.842  -0.391  1.00  0.00           C  
HETATM   20  O2  UNL     1      -6.528  -0.340   0.810  1.00  0.00           O  
HETATM   21  C18 UNL     1      -6.813   0.839   1.533  1.00  0.00           C  
HETATM   22  O3  UNL     1      -5.697   1.652   1.220  1.00  0.00           O  
HETATM   23  C19 UNL     1       2.924   1.076  -0.400  1.00  0.00           C  
HETATM   24  O4  UNL     1       3.402   2.335  -0.132  1.00  0.00           O  
HETATM   25  C20 UNL     1       3.868   2.791   1.098  1.00  0.00           C  
HETATM   26  H1  UNL     1       7.062  -0.107  -1.442  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.159  -1.366  -0.582  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.787  -1.073  -2.360  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.004  -1.977  -1.426  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.638  -2.505  -1.171  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.095   2.683   0.355  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.877   1.988   0.835  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.742  -2.430  -0.070  1.00  0.00           H  
HETATM   34  H9  UNL     1      -2.583  -3.238  -0.659  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.151  -2.878  -0.971  1.00  0.00           H  
HETATM   36  H11 UNL     1      -6.805   0.584   2.618  1.00  0.00           H  
HETATM   37  H12 UNL     1      -7.769   1.304   1.224  1.00  0.00           H  
HETATM   38  H13 UNL     1       4.923   2.446   1.284  1.00  0.00           H  
HETATM   39  H14 UNL     1       3.251   2.457   1.947  1.00  0.00           H  
HETATM   40  H15 UNL     1       3.948   3.910   1.038  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   29
CONECT    5    6    6   30
CONECT    6    7   19
CONECT    7    8   23   23
CONECT    8    9    9   31
CONECT    9   10
CONECT   10   11   11   19
CONECT   11   12   16
CONECT   12   13   13   32
CONECT   13   14   22
CONECT   14   15   15   20
CONECT   15   16   33
CONECT   16   17   17
CONECT   17   18   34
CONECT   18   19   19   35
CONECT   20   21
CONECT   21   22   36   37
CONECT   23   24
CONECT   24   25
CONECT   25   38   39   40
END

HMDB0255726
     RDKit          3D
Norchelerythrine
 40 44  0  0  0  0  0  0  0  0999 V2000
    6.0649   -0.5893   -1.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1148    0.3553   -0.9697 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7789    0.0871   -0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285   -1.1896   -1.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9710   -1.4958   -0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024   -0.5397   -0.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5921    0.7424   -0.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6786    1.6927    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217    1.4210    0.2965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0892    0.1893    0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4609   -0.0140    0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2894    1.0151    0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6500    0.8224    0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1644   -0.4312    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3245   -1.4488    0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9693   -1.2636   -0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1364   -2.2761   -0.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7635   -2.0756   -0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2581   -0.8424   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5275   -0.3402    0.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8128    0.8387    1.5330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6965    1.6517    1.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9238    1.0756   -0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018    2.3355   -0.1323 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8682    2.7907    1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0619   -0.1067   -1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1593   -1.3658   -0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7867   -1.0728   -2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -1.9773   -1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6378   -2.5047   -1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0951    2.6834    0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8774    1.9879    0.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421   -2.4303   -0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5827   -3.2382   -0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1513   -2.8778   -0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8049    0.5838    2.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7693    1.3037    1.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230    2.4460    1.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2513    2.4568    1.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477    3.9105    1.0378 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 14 20  1  0
 20 21  1  0
 21 22  1  0
  7 23  2  0
 23 24  1  0
 24 25  1  0
 23  3  1  0
 19  6  1  0
 19 10  1  0
 16 11  1  0
 22 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  8 31  1  0
 12 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
 25 38  1  0
 25 39  1  0
 25 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Dimethoxy-(1,3)benzodioxolo(5,6-c)phenanthridine	Kegg
Chelerythrine	MeSH
Chelerythrine chloride	MeSH
Chelerythrine sulfate	MeSH
Chelerythrine hydroxide	MeSH

Chemical Formula

C₂₀H₁₅NO₄

Average Molecular Weight

333.343

Monoisotopic Molecular Weight

333.100107967

IUPAC Name

17,18-dimethoxy-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaene

Traditional Name

norchelerythrine

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(C=NC3=C2C=CC2=CC4=C(OCO4)C=C32)=C1OC

InChI Identifier

InChI=1S/C20H15NO4/c1-22-16-6-5-12-13-4-3-11-7-17-18(25-10-24-17)8-14(11)19(13)21-9-15(12)20(16)23-2/h3-9H,10H2,1-2H3

InChI Key

JGUNQXPMULKFNY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Phenanthridines and derivatives

Alternative Parents

Substituents

Phenanthridine
Isoquinoline
Naphthalene
Benzodioxole
Anisole
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Oxacycle
Acetal
Ether
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzophenanthridine alkaloid (CHEBI:31917 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.63	ALOGPS
logP	3.42	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	4.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.81 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.57 m³·mol⁻¹	ChemAxon
Polarizability	35.78 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	211.164	30932474
DeepCCS	[M+Na]+	186.84	30932474
AllCCS	[M+H]+	179.0	32859911
AllCCS	[M+H-H2O]+	175.6	32859911
AllCCS	[M+NH4]+	182.1	32859911
AllCCS	[M+Na]+	183.0	32859911
AllCCS	[M-H]-	183.9	32859911
AllCCS	[M+Na-2H]-	182.9	32859911
AllCCS	[M+HCOO]-	182.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norchelerythrine	COC1=CC=C2C(C=NC3=C2C=CC2=CC4=C(OCO4)C=C32)=C1OC	4297.0	Standard polar	33892256
Norchelerythrine	COC1=CC=C2C(C=NC3=C2C=CC2=CC4=C(OCO4)C=C32)=C1OC	3049.4	Standard non polar	33892256
Norchelerythrine	COC1=CC=C2C(C=NC3=C2C=CC2=CC4=C(OCO4)C=C32)=C1OC	3414.1	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 - Norchelerythrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uxu-0198000000-d52fb7e713edcacd2ceb	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norchelerythrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00024655

Chemspider ID

391829

KEGG Compound ID

C12226

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 Norchelerythrine (HMDB0255726)

MOL for HMDB0255726 (Norchelerythrine)

3D MOL for HMDB0255726 (Norchelerythrine)

3D SDF for HMDB0255726 (Norchelerythrine)

3D-SDF for HMDB0255726 (Norchelerythrine)

PDB for HMDB0255726 (Norchelerythrine)

3D PDB for HMDB0255726 (Norchelerythrine)

SMILES for HMDB0255726 (Norchelerythrine)

INCHI for HMDB0255726 (Norchelerythrine)

Structure for HMDB0255726 (Norchelerythrine)

3D Structure for HMDB0255726 (Norchelerythrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra