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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:37:47 UTC

Update Date

2021-09-26 23:03:13 UTC

HMDB ID

HMDB0251295

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dihydrochelerythrine

Description

Dihydrochelerythrine belongs to the class of organic compounds known as dihydrobenzophenanthridine alkaloids. These are alkaloids containing a dihydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a dihydrophenanthridine moiety. Based on a literature review a significant number of articles have been published on Dihydrochelerythrine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dihydrochelerythrine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dihydrochelerythrine 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

  Mrv1533004191516592D          

 26 30  0  0  0  0            999 V2000
    6.8754    2.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716    1.9694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8774    1.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736    0.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8794    0.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890    1.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927    2.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    2.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1081    2.4521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5176    3.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9043    1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4947    1.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910    0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4967    0.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9063    0.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121    0.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5216    0.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017    0.9298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    2.2233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7254    1.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    2.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101    1.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2870    2.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4908    3.1218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2850    3.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 11 23  2  0  0  0  0
 15 23  1  0  0  0  0
  7 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0251295
     RDKit          3D
Dihydrochelerythrine
 45 49  0  0  0  0  0  0  0  0999 V2000
    6.2716    0.3679   -1.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3350    0.0374   -0.3704 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9691    0.0430   -0.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3956    0.3655   -1.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    0.3613   -1.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961    0.0193   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534   -0.3119    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1145   -0.2922    0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6220   -0.6334    1.7059 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9035   -1.9969    1.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8620   -0.8881    1.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3890   -0.1798    1.4045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8942    0.4103    2.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348    0.0748    0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2435    0.1986   -0.9993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576    0.5051   -2.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2418    0.6875   -2.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0106    0.5580   -1.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3813    0.6997   -1.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1344    0.5262   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5376    0.2106    1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564    0.0645    1.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4005    0.2433    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4998    0.0889    2.1393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7916    0.3384    1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5130    0.6113    0.1945 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9849   -0.0671   -2.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2694   -0.0072   -1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3821    1.4836   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0567    0.6278   -2.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344    0.6189   -2.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8282   -2.2624    1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1045   -2.1540    3.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0261   -2.5724    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954   -1.9643    1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3692   -0.7361    2.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4717    1.3224    2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042    0.9060    3.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544   -0.2705    3.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2558    0.5975   -3.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7119    0.9313   -3.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8236    0.9504   -2.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7792   -0.2685    2.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2495    1.2492    2.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4755   -0.4942    1.7118 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
  7 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
  8  3  1  0
 23 14  1  0
 15  6  1  0
 23 18  1  0
 26 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 22 43  1  0
 25 44  1  0
 25 45  1  0
M  END

  Mrv1533004191516592D          

 26 30  0  0  0  0            999 V2000
    6.8754    2.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716    1.9694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8774    1.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736    0.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8794    0.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890    1.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927    2.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    2.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1081    2.4521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5176    3.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9043    1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4947    1.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910    0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4967    0.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9063    0.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121    0.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5216    0.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017    0.9298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    2.2233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7254    1.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    2.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101    1.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2870    2.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4908    3.1218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2850    3.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 11 23  2  0  0  0  0
 15 23  1  0  0  0  0
  7 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251295

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2C(CN(C)C3=C4C=C5OCOC5=CC4=CC=C23)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H19NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-9H,10-11H2,1-3H3

> <INCHI_KEY>
ALZAZMCIBRHMFF-UHFFFAOYSA-N

> <FORMULA>
C21H19NO4

> <MOLECULAR_WEIGHT>
349.386

> <EXACT_MASS>
349.131408096

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
38.23100420404066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1,3,8,10,12,14,16,18-octaene

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
3.777110031

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.2810494010543207

> <JCHEM_POLAR_SURFACE_AREA>
40.160000000000004

> <JCHEM_REFRACTIVITY>
99.3209

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1,3,8,10,12,14,16,18-octaene

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251295
     RDKit          3D
Dihydrochelerythrine
 45 49  0  0  0  0  0  0  0  0999 V2000
    6.2716    0.3679   -1.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3350    0.0374   -0.3704 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9691    0.0430   -0.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3956    0.3655   -1.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    0.3613   -1.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961    0.0193   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534   -0.3119    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1145   -0.2922    0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6220   -0.6334    1.7059 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9035   -1.9969    1.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8620   -0.8881    1.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3890   -0.1798    1.4045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8942    0.4103    2.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348    0.0748    0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2435    0.1986   -0.9993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576    0.5051   -2.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2418    0.6875   -2.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0106    0.5580   -1.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3813    0.6997   -1.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1344    0.5262   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5376    0.2106    1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564    0.0645    1.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4005    0.2433    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4998    0.0889    2.1393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7916    0.3384    1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5130    0.6113    0.1945 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9849   -0.0671   -2.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2694   -0.0072   -1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3821    1.4836   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0567    0.6278   -2.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344    0.6189   -2.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8282   -2.2624    1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1045   -2.1540    3.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0261   -2.5724    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954   -1.9643    1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3692   -0.7361    2.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4717    1.3224    2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042    0.9060    3.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544   -0.2705    3.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2558    0.5975   -3.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7119    0.9313   -3.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8236    0.9504   -2.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7792   -0.2685    2.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2495    1.2492    2.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4755   -0.4942    1.7118 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
  7 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
  8  3  1  0
 23 14  1  0
 15  6  1  0
 23 18  1  0
 26 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 22 43  1  0
 25 44  1  0
 25 45  1  0
M  END

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      12.834   5.169   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.454   3.676   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.971   3.260   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.591   1.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.108   1.351   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.006   2.426   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.386   3.918   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.284   4.994   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.802   4.577   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.700   5.653   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.421   3.085   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.524   2.009   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.143   0.517   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.661   0.100   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.558   1.176   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.076   0.759   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.974   1.835   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.563   1.736   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.132   3.166   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.052   4.150   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.354   3.327   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.837   3.744   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.939   2.668   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.869   4.335   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.249   5.827   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.732   6.244   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   23                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   11   15                                                  
CONECT   24    7    3   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

COMPND    HMDB0251295
HETATM    1  C1  UNL     1       6.272   0.368  -1.379  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.335   0.037  -0.370  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.969   0.043  -0.600  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.396   0.365  -1.813  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.030   0.361  -1.995  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.196   0.019  -0.918  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.753  -0.312   0.298  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.115  -0.292   0.438  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.622  -0.633   1.706  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.903  -1.997   1.929  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.862  -0.888   1.391  1.00  0.00           C  
HETATM   12  N1  UNL     1      -0.389  -0.180   1.404  1.00  0.00           N  
HETATM   13  C10 UNL     1      -0.894   0.410   2.654  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.035   0.075   0.167  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.244   0.199  -0.999  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.858   0.505  -2.189  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.242   0.687  -2.247  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.011   0.558  -1.114  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.381   0.700  -1.169  1.00  0.00           C  
HETATM   20  C17 UNL     1      -5.134   0.526  -0.029  1.00  0.00           C  
HETATM   21  C18 UNL     1      -4.538   0.211   1.164  1.00  0.00           C  
HETATM   22  C19 UNL     1      -3.156   0.065   1.238  1.00  0.00           C  
HETATM   23  C20 UNL     1      -2.401   0.243   0.114  1.00  0.00           C  
HETATM   24  O3  UNL     1      -5.500   0.089   2.139  1.00  0.00           O  
HETATM   25  C21 UNL     1      -6.792   0.338   1.556  1.00  0.00           C  
HETATM   26  O4  UNL     1      -6.513   0.611   0.194  1.00  0.00           O  
HETATM   27  H1  UNL     1       5.985  -0.067  -2.362  1.00  0.00           H  
HETATM   28  H2  UNL     1       7.269  -0.007  -1.032  1.00  0.00           H  
HETATM   29  H3  UNL     1       6.382   1.484  -1.477  1.00  0.00           H  
HETATM   30  H4  UNL     1       4.057   0.628  -2.636  1.00  0.00           H  
HETATM   31  H5  UNL     1       1.634   0.619  -2.951  1.00  0.00           H  
HETATM   32  H6  UNL     1       4.828  -2.262   1.388  1.00  0.00           H  
HETATM   33  H7  UNL     1       4.104  -2.154   3.023  1.00  0.00           H  
HETATM   34  H8  UNL     1       3.026  -2.572   1.588  1.00  0.00           H  
HETATM   35  H9  UNL     1       0.695  -1.964   1.156  1.00  0.00           H  
HETATM   36  H10 UNL     1       1.369  -0.736   2.361  1.00  0.00           H  
HETATM   37  H11 UNL     1      -1.472   1.322   2.545  1.00  0.00           H  
HETATM   38  H12 UNL     1       0.104   0.906   3.019  1.00  0.00           H  
HETATM   39  H13 UNL     1      -1.054  -0.270   3.470  1.00  0.00           H  
HETATM   40  H14 UNL     1      -0.256   0.598  -3.070  1.00  0.00           H  
HETATM   41  H15 UNL     1      -2.712   0.931  -3.186  1.00  0.00           H  
HETATM   42  H16 UNL     1      -4.824   0.950  -2.141  1.00  0.00           H  
HETATM   43  H17 UNL     1      -2.779  -0.269   2.149  1.00  0.00           H  
HETATM   44  H18 UNL     1      -7.250   1.249   2.041  1.00  0.00           H  
HETATM   45  H19 UNL     1      -7.475  -0.494   1.712  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   30
CONECT    5    6    6   31
CONECT    6    7   15
CONECT    7    8    8   11
CONECT    8    9
CONECT    9   10
CONECT   10   32   33   34
CONECT   11   12   35   36
CONECT   12   13   14
CONECT   13   37   38   39
CONECT   14   15   15   23
CONECT   15   16
CONECT   16   17   17   40
CONECT   17   18   41
CONECT   18   19   19   23
CONECT   19   20   42
CONECT   20   21   21   26
CONECT   21   22   24
CONECT   22   23   23   43
CONECT   24   25
CONECT   25   26   44   45
END

HMDB0251295
     RDKit          3D
Dihydrochelerythrine
 45 49  0  0  0  0  0  0  0  0999 V2000
    6.2716    0.3679   -1.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3350    0.0374   -0.3704 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9691    0.0430   -0.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3956    0.3655   -1.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296    0.3613   -1.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961    0.0193   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534   -0.3119    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1145   -0.2922    0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6220   -0.6334    1.7059 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9035   -1.9969    1.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8620   -0.8881    1.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3890   -0.1798    1.4045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8942    0.4103    2.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348    0.0748    0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2435    0.1986   -0.9993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576    0.5051   -2.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2418    0.6875   -2.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0106    0.5580   -1.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3813    0.6997   -1.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1344    0.5262   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5376    0.2106    1.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564    0.0645    1.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4005    0.2433    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4998    0.0889    2.1393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7916    0.3384    1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5130    0.6113    0.1945 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9849   -0.0671   -2.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2694   -0.0072   -1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3821    1.4836   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0567    0.6278   -2.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344    0.6189   -2.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8282   -2.2624    1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1045   -2.1540    3.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0261   -2.5724    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6954   -1.9643    1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3692   -0.7361    2.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4717    1.3224    2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042    0.9060    3.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544   -0.2705    3.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2558    0.5975   -3.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7119    0.9313   -3.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8236    0.9504   -2.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7792   -0.2685    2.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2495    1.2492    2.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4755   -0.4942    1.7118 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
  7 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
  8  3  1  0
 23 14  1  0
 15  6  1  0
 23 18  1  0
 26 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 22 43  1  0
 25 44  1  0
 25 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₁H₁₉NO₄

Average Molecular Weight

349.386

Monoisotopic Molecular Weight

349.131408096

IUPAC Name

17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1,3,8,10,12,14,16,18-octaene

Traditional Name

17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1,3,8,10,12,14,16,18-octaene

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(CN(C)C3=C4C=C5OCOC5=CC4=CC=C23)=C1OC

InChI Identifier

InChI=1S/C21H19NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-9H,10-11H2,1-3H3

InChI Key

ALZAZMCIBRHMFF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydrobenzophenanthridine alkaloids. These are alkaloids containing a dihydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a dihydrophenanthridine moiety.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Benzophenanthridine alkaloids

Sub Class

Dihydrobenzophenanthridine alkaloids

Direct Parent

Dihydrobenzophenanthridine alkaloids

Alternative Parents

Substituents

Dihydrobenzophenanthridine alkaloid skeleton
Benzoquinoline
Phenanthridine
Naphthalene
Quinoline
Benzodioxole
Anisole
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Aralkylamine
Alkyl aryl ether
Benzenoid
Tertiary amine
Acetal
Ether
Organoheterocyclic compound
Azacycle
Oxacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
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	4.22	ALOGPS
logP	3.78	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	2.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.32 m³·mol⁻¹	ChemAxon
Polarizability	38.23 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]-	217.7	30932474
DeepCCS	[M+Na]+	193.753	30932474
AllCCS	[M+H]+	184.8	32859911
AllCCS	[M+H-H2O]+	182.1	32859911
AllCCS	[M+NH4]+	187.4	32859911
AllCCS	[M+Na]+	188.1	32859911
AllCCS	[M-H]-	183.1	32859911
AllCCS	[M+Na-2H]-	182.0	32859911
AllCCS	[M+HCOO]-	180.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrochelerythrine	COC1=CC=C2C(CN(C)C3=C4C=C5OCOC5=CC4=CC=C23)=C1OC	4435.2	Standard polar	33892256
Dihydrochelerythrine	COC1=CC=C2C(CN(C)C3=C4C=C5OCOC5=CC4=CC=C23)=C1OC	2918.0	Standard non polar	33892256
Dihydrochelerythrine	COC1=CC=C2C(CN(C)C3=C4C=C5OCOC5=CC4=CC=C23)=C1OC	3302.2	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 - Dihydrochelerythrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05o0-0119000000-a7e228c74d5cd70ed883	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrochelerythrine 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 - Dihydrochelerythrine 10V, Positive-QTOF	splash10-0udi-0009000000-ddec77d09295f87305e1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrochelerythrine 20V, Positive-QTOF	splash10-0udi-0009000000-0ca250fd98898b7978d6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrochelerythrine 40V, Positive-QTOF	splash10-0r0r-0049000000-7ffef18a00027ec1fd8d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrochelerythrine 10V, Negative-QTOF	splash10-0002-0009000000-2a2e10ff1b72ae5182ee	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrochelerythrine 20V, Negative-QTOF	splash10-0002-0009000000-3b8d9a8817aff486e360	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrochelerythrine 40V, Negative-QTOF	splash10-0uki-0095000000-2d4053bf75a3a068058d	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

Not Available

Chemspider ID

425346

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

485077

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 Dihydrochelerythrine (HMDB0251295)

MOL for HMDB0251295 (Dihydrochelerythrine)

3D MOL for HMDB0251295 (Dihydrochelerythrine)

3D SDF for HMDB0251295 (Dihydrochelerythrine)

3D-SDF for HMDB0251295 (Dihydrochelerythrine)

PDB for HMDB0251295 (Dihydrochelerythrine)

3D PDB for HMDB0251295 (Dihydrochelerythrine)

SMILES for HMDB0251295 (Dihydrochelerythrine)

INCHI for HMDB0251295 (Dihydrochelerythrine)

Structure for HMDB0251295 (Dihydrochelerythrine)

3D Structure for HMDB0251295 (Dihydrochelerythrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra