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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:45 UTC

Update Date

2022-03-07 02:52:29 UTC

HMDB ID

HMDB0030258

Secondary Accession Numbers

HMDB30258

Metabolite Identification

Common Name

(+)-Erythraline

Description

(+)-Erythraline is found in green vegetables. (+)-Erythraline is an alkaloid from Erythrina glauca (gallito) Alitretinoin (9-cis-retinoic acid) is a naturally-occurring endogenous retinoid indicated for topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma. Alitretinoin inhibits the growth of Kaposi's sarcoma (KS) cells in vitro. Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately control anterior/posterior patterning in early developmental stages. Retinoic acid acts by binding to heterodimers of the retinoic acid receptor (RAR) and the retinoid X receptor (RXR), which then bind to retinoic acid response elements (RAREs) in the regulatory regions of direct targets (including Hox genes), thereby activating gene transcription. Retinoic acid receptors mediate transcription of different sets of genes of cell differentiation, thus it also depends on the target cells. (+)-Erythraline is one of the target genes is the gene of the retinoic acid receptor itself which occurs during positive regulation. Control of retinoic acid levels is maintained by a suite of proteins. Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912 ). It is an important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth and embryonic development. (+)-Erythraline is an excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute)

Structure

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

HMDB0030258
     RDKit          3D
(+)-Erythraline
 41 45  0  0  0  0  0  0  0  0999 V2000
   -3.9988    1.9614    2.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005    2.2765    1.6805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3209    1.4533    0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475    2.2086   -0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367    1.4267   -1.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088    0.0004   -1.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138   -1.1352   -1.8993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0610   -2.3203   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0996   -1.7097    0.2573 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2707   -2.5155    1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1280   -2.7296    0.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6320   -1.4217    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0217   -1.2472   -0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5669   -0.0609   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7333    1.0230   -0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3826    0.8766   -0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8352   -0.3537   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585   -0.3663    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0751    0.6659    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5795    2.0508   -1.1322 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    1.7590   -0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8780    0.3335   -0.7253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0816    0.9008    2.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6590    2.0550    1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3892    2.6451    2.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1688    0.7591    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2087    3.2199   -0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884    1.7700   -2.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623   -1.1639   -2.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917   -2.6768   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8372   -3.1078   -1.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7864   -3.5091    1.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1815   -2.0811    2.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071   -3.0999    1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2276   -3.5206   -0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -2.1211    0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651    1.7331   -0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1907    0.2555    2.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2636    1.4581    1.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0299    2.1585    0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6668    2.1494   -1.4148 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  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  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 19  3  1  0
 18  6  1  0
 18  9  1  0
 17 12  1  0
 22 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 16 37  1  0
 19 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
M  END

  Mrv0541 02241214272D          

 22 26  0  0  0  0            999 V2000
   -0.4946    1.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3196    1.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946   -1.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796   -1.4846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4747   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796   -0.1646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071   -1.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497   -0.4121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4747   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4747    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071    1.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 21  1  0  0  0  0
  3  4  2  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 17  1  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
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030258

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1CC23N(CC=C2C=C1)CCC1=C3C=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO3/c1-20-14-3-2-13-5-7-19-6-4-12-8-16-17(22-11-21-16)9-15(12)18(13,19)10-14/h2-3,5,8-9,14H,4,6-7,10-11H2,1H3

> <INCHI_KEY>
TVOFUERNMZTYRM-UHFFFAOYSA-N

> <FORMULA>
C18H19NO3

> <MOLECULAR_WEIGHT>
297.3484

> <EXACT_MASS>
297.136493479

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.08138552590208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <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(10),3,8,15,17-pentaene

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.998125228333333

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.00959782993135

> <JCHEM_POLAR_SURFACE_AREA>
30.93

> <JCHEM_REFRACTIVITY>
85.27970000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-methoxy-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2(10),3,8,15,17-pentaene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030258
     RDKit          3D
(+)-Erythraline
 41 45  0  0  0  0  0  0  0  0999 V2000
   -3.9988    1.9614    2.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005    2.2765    1.6805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3209    1.4533    0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475    2.2086   -0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367    1.4267   -1.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088    0.0004   -1.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138   -1.1352   -1.8993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0610   -2.3203   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0996   -1.7097    0.2573 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2707   -2.5155    1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1280   -2.7296    0.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6320   -1.4217    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0217   -1.2472   -0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5669   -0.0609   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7333    1.0230   -0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3826    0.8766   -0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8352   -0.3537   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585   -0.3663    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0751    0.6659    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5795    2.0508   -1.1322 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    1.7590   -0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8780    0.3335   -0.7253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0816    0.9008    2.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6590    2.0550    1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3892    2.6451    2.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1688    0.7591    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2087    3.2199   -0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884    1.7700   -2.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623   -1.1639   -2.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917   -2.6768   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8372   -3.1078   -1.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7864   -3.5091    1.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1815   -2.0811    2.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071   -3.0999    1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2276   -3.5206   -0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -2.1211    0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651    1.7331   -0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1907    0.2555    2.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2636    1.4581    1.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0299    2.1585    0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6668    2.1494   -1.4148 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  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  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 19  3  1  0
 18  6  1  0
 18  9  1  0
 17 12  1  0
 22 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 16 37  1  0
 19 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.923   3.079   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.463   3.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.923  -3.079   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.309  -2.309   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.695  -2.771   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.619  -1.539   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.695  -0.307   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.309  -0.769   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.923  -0.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.461  -0.769   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.461  -2.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.693  -3.079   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.079  -2.309   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.079  -0.769   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.619  -0.769   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.619   0.769   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.693  -0.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.079   0.769   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.079   2.309   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.693   3.079   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.461   2.309   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.461   0.769   0.000  0.00  0.00           C+0
CONECT    1    2   21                                                       
CONECT    2    1                                                            
CONECT    3    4   11                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    4    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11    3   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   18                                                       
CONECT   17   10   14   18   22                                             
CONECT   18   16   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21    1   20   22                                                  
CONECT   22   17   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

COMPND    HMDB0030258
HETATM    1  C1  UNL     1      -3.999   1.961   2.066  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.700   2.277   1.680  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.321   1.453   0.658  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.048   2.209  -0.608  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.537   1.427  -1.556  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.309   0.000  -1.277  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.514  -1.135  -1.899  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.061  -2.320  -1.079  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.100  -1.710   0.257  1.00  0.00           N  
HETATM   10  C8  UNL     1      -0.271  -2.515   1.100  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.128  -2.730   0.605  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.632  -1.422   0.147  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.022  -1.247  -0.046  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.567  -0.061  -0.471  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.733   1.023  -0.727  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.383   0.877  -0.546  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.835  -0.354  -0.107  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.658  -0.366   0.049  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.075   0.666   1.019  1.00  0.00           C  
HETATM   20  O2  UNL     1       3.580   2.051  -1.132  1.00  0.00           O  
HETATM   21  C18 UNL     1       4.915   1.759  -0.704  1.00  0.00           C  
HETATM   22  O3  UNL     1       4.878   0.333  -0.725  1.00  0.00           O  
HETATM   23  H1  UNL     1      -4.082   0.901   2.416  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.659   2.055   1.158  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.389   2.645   2.843  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.169   0.759   0.424  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.209   3.220  -0.803  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.288   1.770  -2.522  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.962  -1.164  -2.905  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.092  -2.677  -1.387  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.837  -3.108  -1.083  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.786  -3.509   1.185  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.182  -2.081   2.127  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.707  -3.100   1.496  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.228  -3.521  -0.168  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.632  -2.121   0.166  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.765   1.733  -0.751  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.191   0.256   2.051  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.264   1.458   1.025  1.00  0.00           H  
HETATM   40  H18 UNL     1       5.030   2.158   0.321  1.00  0.00           H  
HETATM   41  H19 UNL     1       5.667   2.149  -1.415  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4   19   26
CONECT    4    5    5   27
CONECT    5    6   28
CONECT    6    7    7   18
CONECT    7    8   29
CONECT    8    9   30   31
CONECT    9   10   18
CONECT   10   11   32   33
CONECT   11   12   34   35
CONECT   12   13   13   17
CONECT   13   14   36
CONECT   14   15   15   22
CONECT   15   16   20
CONECT   16   17   17   37
CONECT   17   18
CONECT   18   19
CONECT   19   38   39
CONECT   20   21
CONECT   21   22   40   41
END

HMDB0030258
     RDKit          3D
(+)-Erythraline
 41 45  0  0  0  0  0  0  0  0999 V2000
   -3.9988    1.9614    2.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005    2.2765    1.6805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3209    1.4533    0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475    2.2086   -0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367    1.4267   -1.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088    0.0004   -1.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138   -1.1352   -1.8993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0610   -2.3203   -1.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0996   -1.7097    0.2573 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2707   -2.5155    1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1280   -2.7296    0.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6320   -1.4217    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0217   -1.2472   -0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5669   -0.0609   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7333    1.0230   -0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3826    0.8766   -0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8352   -0.3537   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585   -0.3663    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0751    0.6659    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5795    2.0508   -1.1322 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    1.7590   -0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8780    0.3335   -0.7253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0816    0.9008    2.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6590    2.0550    1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3892    2.6451    2.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1688    0.7591    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2087    3.2199   -0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884    1.7700   -2.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623   -1.1639   -2.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0917   -2.6768   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8372   -3.1078   -1.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7864   -3.5091    1.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1815   -2.0811    2.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7071   -3.0999    1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2276   -3.5206   -0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -2.1211    0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651    1.7331   -0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1907    0.2555    2.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2636    1.4581    1.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0299    2.1585    0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6668    2.1494   -1.4148 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  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  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 19  3  1  0
 18  6  1  0
 18  9  1  0
 17 12  1  0
 22 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 16 37  1  0
 19 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Erythraline	HMDB

Chemical Formula

C₁₈H₁₉NO₃

Average Molecular Weight

297.3484

Monoisotopic Molecular Weight

297.136493479

IUPAC Name

19-methoxy-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2(10),3,8,15,17-pentaene

Traditional Name

19-methoxy-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2(10),3,8,15,17-pentaene

CAS Registry Number

466-77-3

SMILES

COC1CC23N(CC=C2C=C1)CCC1=C3C=C2OCOC2=C1

InChI Identifier

InChI=1S/C18H19NO3/c1-20-14-3-2-13-5-7-19-6-4-12-8-16-17(22-11-21-16)9-15(12)18(13,19)10-14/h2-3,5,8-9,14H,4,6-7,10-11H2,1H3

InChI Key

TVOFUERNMZTYRM-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
Pyrroline
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Dialkyl ether
Ether
Azacycle
Acetal
Organoheterocyclic compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030258)
Cell membrane (HMDB: HMDB0030258)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030258)

Source

Endogenous

Endogenous (HMDB: HMDB0030258)

Plant

Plant (HMDB: HMDB0030258)

Exogenous

Food

Food (HMDB: HMDB0030258)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0030258)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	120 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	6.30	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.05 g/L	ALOGPS
logP	2.01	ALOGPS
logP	2	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	9.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.93 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.28 m³·mol⁻¹	ChemAxon
Polarizability	32.08 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.023	31661259
DarkChem	[M-H]-	168.108	31661259
DeepCCS	[M-2H]-	201.543	30932474
DeepCCS	[M+Na]+	177.108	30932474
AllCCS	[M+H]+	170.7	32859911
AllCCS	[M+H-H2O]+	167.2	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.8	32859911
AllCCS	[M-H]-	177.5	32859911
AllCCS	[M+Na-2H]-	176.8	32859911
AllCCS	[M+HCOO]-	176.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-Erythraline	COC1CC23N(CC=C2C=C1)CCC1=C3C=C2OCOC2=C1	4076.7	Standard polar	33892256
(+)-Erythraline	COC1CC23N(CC=C2C=C1)CCC1=C3C=C2OCOC2=C1	2292.9	Standard non polar	33892256
(+)-Erythraline	COC1CC23N(CC=C2C=C1)CCC1=C3C=C2OCOC2=C1	2610.7	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 - (+)-Erythraline GC-MS (Non-derivatized) - 70eV, Positive	splash10-015i-0190000000-31a215c71d077d41cd3c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Erythraline 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 - (+)-Erythraline 10V, Positive-QTOF	splash10-0002-0090000000-4ed4932343e54c47b889	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Erythraline 20V, Positive-QTOF	splash10-00kb-0090000000-3f45afeb82d24f91e26f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Erythraline 40V, Positive-QTOF	splash10-052o-1690000000-ea46bd1a5bb5184fcba8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Erythraline 10V, Negative-QTOF	splash10-0002-0090000000-e65fe867119975c81d74	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Erythraline 20V, Negative-QTOF	splash10-0002-0090000000-118fb68f55dae0d84902	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Erythraline 40V, Negative-QTOF	splash10-0f89-1190000000-17347a064f6a1d40eb77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Erythraline 10V, Positive-QTOF	splash10-0002-0090000000-620f87966eb750d6f48d	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Erythraline 20V, Positive-QTOF	splash10-00kb-0090000000-e0c9e93842a5dcbc6faf	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Erythraline 40V, Positive-QTOF	splash10-0159-0290000000-50da91a2cb3d44278298	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Erythraline 10V, Negative-QTOF	splash10-0002-0090000000-f0a7b42101b1968126a5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Erythraline 20V, Negative-QTOF	splash10-0002-0090000000-6e7152719730c22b3e4a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Erythraline 40V, Negative-QTOF	splash10-001v-0190000000-8022183ddbfa6a633fa5	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB002082

KNApSAcK ID

C00027355

Chemspider ID

26504826

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12308897

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1043701

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Holland LZ: Developmental biology: a chordate with a difference. Nature. 2007 May 10;447(7141):153-5. [PubMed:17495912 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (+)-Erythraline (HMDB0030258)

MOL for HMDB0030258 ((+)-Erythraline)

3D MOL for HMDB0030258 ((+)-Erythraline)

3D SDF for HMDB0030258 ((+)-Erythraline)

3D-SDF for HMDB0030258 ((+)-Erythraline)

PDB for HMDB0030258 ((+)-Erythraline)

3D PDB for HMDB0030258 ((+)-Erythraline)

SMILES for HMDB0030258 ((+)-Erythraline)

INCHI for HMDB0030258 ((+)-Erythraline)

Structure for HMDB0030258 ((+)-Erythraline)

3D Structure for HMDB0030258 ((+)-Erythraline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra