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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:19 UTC

Update Date

2022-03-07 02:52:27 UTC

HMDB ID

HMDB0030181

Secondary Accession Numbers

HMDB30181

Metabolite Identification

Common Name

Erythratine

Description

Erythratine belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof. Based on a literature review a significant number of articles have been published on Erythratine.

Structure

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

HMDB0030181
     RDKit          3D
Erythratine
 44 48  0  0  0  0  0  0  0  0999 V2000
   -4.1952    1.5783    1.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8821    1.7485    1.0926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4769    0.7759    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3749   -0.0064    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4591   -0.6966   -0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8184   -0.4553   -1.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5884    0.4945   -2.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984    1.4640   -1.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4783    2.6479   -0.9943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0973   -1.5592   -2.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5309   -2.7091   -1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420   -2.1355   -0.0595 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4743   -2.7768    0.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0827   -1.9551    1.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162   -0.7916    1.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922   -0.3785    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4961    0.6885    0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230    1.2841   -0.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    0.8439   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9193   -0.2127    0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4876    2.3245   -0.8675 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5142    2.6417    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039    1.3626    0.6805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8603    1.6358    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4373    2.2627    2.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2747    0.5246    1.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3755    0.1050    0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8268   -0.7911    1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8251    0.6652    1.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8273    0.6393   -3.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2074    1.7866   -1.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0531    2.7524   -0.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959   -1.6965   -3.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167   -1.4208   -2.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5734   -2.9749   -1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1490   -3.5799   -1.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0497   -3.7351    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3259   -3.0089   -0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016   -2.5590    2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3630   -1.6267    2.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5657   -0.8767    2.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9075    1.3738   -1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0819    3.3355    0.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3992    3.0112   -0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 20 15  1  0
 12  5  1  0
 23 17  1  0
 20  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  0
  9 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
 14 39  1  0
 14 40  1  0
 16 41  1  0
 19 42  1  0
 22 43  1  0
 22 44  1  0
M  END


  Mrv0541 05061305032D          

 23 27  0  0  0  0            999 V2000
    3.7329    1.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849   -1.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0436    0.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9770   -1.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0380    0.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414   -0.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226    0.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1541    0.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7654    0.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3335   -0.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8495    1.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0740    0.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829    1.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6899   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305    0.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4995    1.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2661    0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176   -0.2731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4913    2.4936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3245    1.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.1529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0952    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  3  1  0  0  0  0
 12  7  2  0  0  0  0
 13  8  2  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
 16 15  2  0  0  0  0
 17  9  1  0  0  0  0
 17 14  1  0  0  0  0
 18  9  1  0  0  0  0
 18 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19  4  1  0  0  0  0
 19  5  1  0  0  0  0
 19 18  1  0  0  0  0
 20 14  1  0  0  0  0
 21  1  1  0  0  0  0
 21 17  1  0  0  0  0
 22 10  1  0  0  0  0
 22 15  1  0  0  0  0
 23 10  1  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030181

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1CC23N(CCC2=CC1O)CCC1=CC2=C(OCO2)C=C31

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO4/c1-21-17-9-18-12(7-14(17)20)3-5-19(18)4-2-11-6-15-16(8-13(11)18)23-10-22-15/h6-8,14,17,20H,2-5,9-10H2,1H3

> <INCHI_KEY>
ZIAIDGYDHGYWBH-UHFFFAOYSA-N

> <FORMULA>
C18H21NO4

> <MOLECULAR_WEIGHT>
315.3636

> <EXACT_MASS>
315.147058165

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.54438028778797

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
19-methoxy-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,16-tetraen-18-ol

> <ALOGPS_LOGP>
0.65

> <JCHEM_LOGP>
1.129235817999999

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.805416192939873

> <JCHEM_PKA_STRONGEST_BASIC>
8.55170917590821

> <JCHEM_POLAR_SURFACE_AREA>
51.16000000000001

> <JCHEM_REFRACTIVITY>
85.6786

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-methoxy-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,16-tetraen-18-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030181
     RDKit          3D
Erythratine
 44 48  0  0  0  0  0  0  0  0999 V2000
   -4.1952    1.5783    1.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8821    1.7485    1.0926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4769    0.7759    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3749   -0.0064    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4591   -0.6966   -0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8184   -0.4553   -1.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5884    0.4945   -2.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984    1.4640   -1.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4783    2.6479   -0.9943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0973   -1.5592   -2.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5309   -2.7091   -1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420   -2.1355   -0.0595 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4743   -2.7768    0.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0827   -1.9551    1.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162   -0.7916    1.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922   -0.3785    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4961    0.6885    0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230    1.2841   -0.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    0.8439   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9193   -0.2127    0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4876    2.3245   -0.8675 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5142    2.6417    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039    1.3626    0.6805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8603    1.6358    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4373    2.2627    2.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2747    0.5246    1.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3755    0.1050    0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8268   -0.7911    1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8251    0.6652    1.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8273    0.6393   -3.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2074    1.7866   -1.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0531    2.7524   -0.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959   -1.6965   -3.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167   -1.4208   -2.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5734   -2.9749   -1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1490   -3.5799   -1.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0497   -3.7351    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3259   -3.0089   -0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016   -2.5590    2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3630   -1.6267    2.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5657   -0.8767    2.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9075    1.3738   -1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0819    3.3355    0.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3992    3.0112   -0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 20 15  1  0
 12  5  1  0
 23 17  1  0
 20  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  0
  9 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
 14 39  1  0
 14 40  1  0
 16 41  1  0
 19 42  1  0
 22 43  1  0
 22 44  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.968   3.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.332  -2.283   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.081   1.641   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.824  -1.972   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.071   0.108   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.864  -1.444   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.348   3.308   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.896   1.479   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.021   0.833   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.895   1.182   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.356  -1.133   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.586   1.970   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.871   0.329   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.888   3.317   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.888  -0.294   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.404   1.168   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.666   1.987   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.363   0.640   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.340  -0.510   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       4.650   4.655   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.206   1.996   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.428  -0.285   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.644   2.080   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    4   11                                                       
CONECT    3    5   12                                                       
CONECT    4    2   19                                                       
CONECT    5    3   19                                                       
CONECT    6   11   15                                                       
CONECT    7   12   14                                                       
CONECT    8   13   16                                                       
CONECT    9   17   18                                                       
CONECT   10   22   23                                                       
CONECT   11    2    6   13                                                  
CONECT   12    3    7   18                                                  
CONECT   13    8   11   18                                                  
CONECT   14    7   17   20                                                  
CONECT   15    6   16   22                                                  
CONECT   16    8   15   23                                                  
CONECT   17    9   14   21                                                  
CONECT   18    9   12   13   19                                             
CONECT   19    4    5   18                                                  
CONECT   20   14                                                            
CONECT   21    1   17                                                       
CONECT   22   10   15                                                       
CONECT   23   10   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0030181
HETATM    1  C1  UNL     1      -4.195   1.578   1.509  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.882   1.749   1.093  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.477   0.776   0.178  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.375  -0.006   0.787  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.459  -0.697  -0.173  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.818  -0.455  -1.599  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.588   0.494  -2.062  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.198   1.464  -1.113  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.478   2.648  -0.994  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.097  -1.559  -2.270  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.531  -2.709  -1.388  1.00  0.00           C  
HETATM   12  N1  UNL     1      -0.542  -2.136  -0.060  1.00  0.00           N  
HETATM   13  C10 UNL     1       0.474  -2.777   0.690  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.083  -1.955   1.804  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.716  -0.792   1.077  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.992  -0.378   1.379  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.496   0.688   0.658  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.723   1.284  -0.311  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.429   0.844  -0.597  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.919  -0.213   0.111  1.00  0.00           C  
HETATM   21  O3  UNL     1       3.488   2.324  -0.867  1.00  0.00           O  
HETATM   22  C18 UNL     1       4.514   2.642   0.085  1.00  0.00           C  
HETATM   23  O4  UNL     1       4.704   1.363   0.681  1.00  0.00           O  
HETATM   24  H1  UNL     1      -4.860   1.636   0.633  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.437   2.263   2.320  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.275   0.525   1.882  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.375   0.105   0.037  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.827  -0.791   1.431  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.825   0.665   1.511  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.827   0.639  -3.113  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.207   1.787  -1.513  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.053   2.752  -0.114  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.396  -1.697  -3.324  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.017  -1.421  -2.220  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.573  -2.975  -1.711  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.149  -3.580  -1.472  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.050  -3.735   1.099  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.326  -3.009  -0.015  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.902  -2.559   2.238  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.363  -1.627   2.553  1.00  0.00           H  
HETATM   41  H18 UNL     1       3.566  -0.877   2.150  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.907   1.374  -1.374  1.00  0.00           H  
HETATM   43  H20 UNL     1       4.082   3.336   0.822  1.00  0.00           H  
HETATM   44  H21 UNL     1       5.399   3.011  -0.436  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    8   27
CONECT    4    5   28   29
CONECT    5    6   12   20
CONECT    6    7    7   10
CONECT    7    8   30
CONECT    8    9   31
CONECT    9   32
CONECT   10   11   33   34
CONECT   11   12   35   36
CONECT   12   13
CONECT   13   14   37   38
CONECT   14   15   39   40
CONECT   15   16   16   20
CONECT   16   17   41
CONECT   17   18   18   23
CONECT   18   19   21
CONECT   19   20   20   42
CONECT   21   22
CONECT   22   23   43   44
END

HMDB0030181
     RDKit          3D
Erythratine
 44 48  0  0  0  0  0  0  0  0999 V2000
   -4.1952    1.5783    1.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8821    1.7485    1.0926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4769    0.7759    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3749   -0.0064    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4591   -0.6966   -0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8184   -0.4553   -1.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5884    0.4945   -2.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1984    1.4640   -1.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4783    2.6479   -0.9943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0973   -1.5592   -2.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5309   -2.7091   -1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420   -2.1355   -0.0595 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4743   -2.7768    0.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0827   -1.9551    1.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7162   -0.7916    1.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922   -0.3785    1.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4961    0.6885    0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230    1.2841   -0.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    0.8439   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9193   -0.2127    0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4876    2.3245   -0.8675 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5142    2.6417    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039    1.3626    0.6805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8603    1.6358    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4373    2.2627    2.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2747    0.5246    1.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3755    0.1050    0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8268   -0.7911    1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8251    0.6652    1.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8273    0.6393   -3.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2074    1.7866   -1.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0531    2.7524   -0.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959   -1.6965   -3.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0167   -1.4208   -2.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5734   -2.9749   -1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1490   -3.5799   -1.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0497   -3.7351    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3259   -3.0089   -0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016   -2.5590    2.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3630   -1.6267    2.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5657   -0.8767    2.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9075    1.3738   -1.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0819    3.3355    0.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3992    3.0112   -0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 20 15  1  0
 12  5  1  0
 23 17  1  0
 20  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  0
  9 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
 14 39  1  0
 14 40  1  0
 16 41  1  0
 19 42  1  0
 22 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,6-Didehydro-3-methoxy-15,16-[methylenebis(oxy)]erythrinan-2-ol, 9ci	HMDB

Chemical Formula

C₁₈H₂₁NO₄

Average Molecular Weight

315.3636

Monoisotopic Molecular Weight

315.147058165

IUPAC Name

19-methoxy-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,16-tetraen-18-ol

Traditional Name

19-methoxy-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,16-tetraen-18-ol

CAS Registry Number

5550-20-9

SMILES

COC1CC23N(CCC2=CC1O)CCC1=CC2=C(OCO2)C=C31

InChI Identifier

InChI=1S/C18H21NO4/c1-21-17-9-18-12(7-14(17)20)3-5-19(18)4-2-11-6-15-16(8-13(11)18)23-10-22-15/h6-8,14,17,20H,2-5,9-10H2,1H3

InChI Key

ZIAIDGYDHGYWBH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Erythrina alkaloids

Sub Class

Erythrinanes

Direct Parent

Erythrinanes

Alternative Parents

Substituents

Erythrinane skeleton
Tetrahydroisoquinoline
Benzodioxole
Indole or derivatives
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Dialkyl ether
Ether
Azacycle
Acetal
Organoheterocyclic compound
Organopnictogen compound
Amine
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030181)
Cytoplasm (HMDB: HMDB0030181)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030181)

Source

Endogenous

Endogenous (HMDB: HMDB0030181)

Plant

Plant (HMDB: HMDB0030181)

Exogenous

Food

Food (HMDB: HMDB0030181)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0030181)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	170 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.94 g/L	ALOGPS
logP	0.65	ALOGPS
logP	1.13	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.81	ChemAxon
pKa (Strongest Basic)	8.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.16 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.68 m³·mol⁻¹	ChemAxon
Polarizability	33.54 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
DarkChem	[M+H]+	173.185	31661259
DarkChem	[M-H]-	171.015	31661259
DeepCCS	[M-2H]-	203.384	30932474
DeepCCS	[M+Na]+	178.611	30932474
AllCCS	[M+H]+	175.2	32859911
AllCCS	[M+H-H2O]+	172.0	32859911
AllCCS	[M+NH4]+	178.2	32859911
AllCCS	[M+Na]+	179.1	32859911
AllCCS	[M-H]-	180.2	32859911
AllCCS	[M+Na-2H]-	179.7	32859911
AllCCS	[M+HCOO]-	179.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.24 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0186 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.98 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	71.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1338.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	203.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	140.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	54.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	283.1 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	337.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	385.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	699.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	292.6 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	1153.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	226.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	421.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	320.6 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	106.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Erythratine	COC1CC23N(CCC2=CC1O)CCC1=CC2=C(OCO2)C=C31	4008.0	Standard polar	33892256
Erythratine	COC1CC23N(CCC2=CC1O)CCC1=CC2=C(OCO2)C=C31	2452.6	Standard non polar	33892256
Erythratine	COC1CC23N(CCC2=CC1O)CCC1=CC2=C(OCO2)C=C31	2700.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Erythratine,1TMS,isomer #1	COC1CC23C(=CC1O[Si](C)(C)C)CCN2CCC1=CC2=C(C=C13)OCO2	2655.0	Semi standard non polar	33892256
Erythratine,1TBDMS,isomer #1	COC1CC23C(=CC1O[Si](C)(C)C(C)(C)C)CCN2CCC1=CC2=C(C=C13)OCO2	2890.6	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 - Erythratine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01t9-1090000000-9cd4cf79ce23bfbadc35	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythratine GC-MS (1 TMS) - 70eV, Positive	splash10-024i-8197000000-e19e4017d53cd32d4040	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erythratine 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 - Erythratine 10V, Positive-QTOF	splash10-014i-0039000000-9205b955c498a6f200a3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythratine 20V, Positive-QTOF	splash10-014i-0095000000-733520a7d0c129d6f784	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythratine 40V, Positive-QTOF	splash10-0fbc-0290000000-0e2a6170b2dbcb93ed8a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythratine 10V, Negative-QTOF	splash10-03di-0029000000-10c7bdc4d4ddffd29689	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythratine 20V, Negative-QTOF	splash10-03di-1097000000-11c6f1aedae1f3bba625	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythratine 40V, Negative-QTOF	splash10-05mk-3090000000-01ad606cea224e556995	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythratine 10V, Negative-QTOF	splash10-03di-0009000000-a9f6ec6e6fe2a282293c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythratine 20V, Negative-QTOF	splash10-03di-0059000000-84c3094f8869db38bf17	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythratine 40V, Negative-QTOF	splash10-01ta-0091000000-47209987c6645dcbe456	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythratine 10V, Positive-QTOF	splash10-014i-0009000000-135924c69299cfc5fa80	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythratine 20V, Positive-QTOF	splash10-014i-0059000000-dce2672b4f4a5e37d393	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erythratine 40V, Positive-QTOF	splash10-014i-0191000000-0adce574bfeb3992f6e5	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB001997

KNApSAcK ID

C00030212

Chemspider ID

536982

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

617879

PDB ID

Not Available

ChEBI ID

175047

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1817711

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Erythratine (HMDB0030181)

MOL for HMDB0030181 (Erythratine)

3D MOL for HMDB0030181 (Erythratine)

3D SDF for HMDB0030181 (Erythratine)

3D-SDF for HMDB0030181 (Erythratine)

PDB for HMDB0030181 (Erythratine)

3D PDB for HMDB0030181 (Erythratine)

SMILES for HMDB0030181 (Erythratine)

INCHI for HMDB0030181 (Erythratine)

Structure for HMDB0030181 (Erythratine)

3D Structure for HMDB0030181 (Erythratine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra