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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:25:00 UTC

Update Date

2021-09-26 23:01:52 UTC

HMDB ID

HMDB0250413

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Combretastatin A4

Description

2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenol belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Based on a literature review very few articles have been published on 2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Combretastatin a4 is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Combretastatin A4 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

HMDB0250413
     RDKit          3D
Combretastatin A4
 43 44  0  0  0  0  0  0  0  0999 V2000
    3.6014   -2.0695    6.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -2.4146    5.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1371   -1.9330    3.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048   -1.0231    4.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4418   -0.5668    2.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7609   -0.9839    1.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0669   -0.5315    0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0009    0.2052    0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7128    0.6779   -0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1996    0.5062   -1.9325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8736    0.9378   -3.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3221    0.7538   -4.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7552    0.2541   -4.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0793    1.5384   -2.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316    2.0001   -3.9872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8267    1.1185   -4.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6636    1.7469   -1.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8077    2.3125   -1.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9070    2.8461   -1.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9278    1.2880   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8013   -1.9058    1.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4800   -2.3727    2.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4570   -3.2395    2.5454 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4149   -2.2761    7.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -0.9479    6.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117   -2.4720    6.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8104   -0.6646    5.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333    0.1570    3.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814   -0.8502   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3935    0.4951    1.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    0.0351   -2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7362    0.4643   -4.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9572    0.6731   -5.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488   -0.8818   -4.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6942    0.8996   -5.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8425    1.5444   -4.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7812    0.1522   -3.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7510    2.9132   -1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8182    3.9333   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4123    2.3249   -0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    1.4390    0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0724   -2.2548    0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1041   -3.8290    2.3401 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  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
  6 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 20  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 30  1  0
 10 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 23 43  1  0
M  END

  Mrv1533004241504102D          

 23 24  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
  9 20  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250413

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=CC2=CC(OC)=C(OC)C(OC)=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3

> <INCHI_KEY>
HVXBOLULGPECHP-UHFFFAOYSA-N

> <FORMULA>
C18H20O5

> <MOLECULAR_WEIGHT>
316.353

> <EXACT_MASS>
316.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.631807204728155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenol

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
3.378836467

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.842875210517926

> <JCHEM_PKA_STRONGEST_BASIC>
-4.312434920114545

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
89.3465

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
combretastatin A-4

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250413
     RDKit          3D
Combretastatin A4
 43 44  0  0  0  0  0  0  0  0999 V2000
    3.6014   -2.0695    6.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -2.4146    5.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1371   -1.9330    3.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048   -1.0231    4.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4418   -0.5668    2.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7609   -0.9839    1.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0669   -0.5315    0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0009    0.2052    0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7128    0.6779   -0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1996    0.5062   -1.9325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8736    0.9378   -3.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3221    0.7538   -4.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7552    0.2541   -4.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0793    1.5384   -2.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316    2.0001   -3.9872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8267    1.1185   -4.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6636    1.7469   -1.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8077    2.3125   -1.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9070    2.8461   -1.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9278    1.2880   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8013   -1.9058    1.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4800   -2.3727    2.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4570   -3.2395    2.5454 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4149   -2.2761    7.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -0.9479    6.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117   -2.4720    6.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8104   -0.6646    5.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333    0.1570    3.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814   -0.8502   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3935    0.4951    1.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    0.0351   -2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7362    0.4643   -4.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9572    0.6731   -5.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488   -0.8818   -4.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6942    0.8996   -5.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8425    1.5444   -4.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7812    0.1522   -3.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7510    2.9132   -1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8182    3.9333   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4123    2.3249   -0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    1.4390    0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0724   -2.2548    0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1041   -3.8290    2.3401 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  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
  6 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 20  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 30  1  0
 10 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 23 43  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17    9                                                       
CONECT   21    6   22                                                       
CONECT   22   21    3   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0250413
HETATM    1  C1  UNL     1       3.601  -2.070   6.364  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.827  -2.415   5.036  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.137  -1.933   3.954  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.105  -1.023   4.044  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.442  -0.567   2.924  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.761  -0.984   1.653  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.067  -0.531   0.456  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.001   0.205   0.525  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.713   0.678  -0.677  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.200   0.506  -1.933  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.874   0.938  -3.098  1.00  0.00           C  
HETATM   12  O2  UNL     1      -0.322   0.754  -4.295  1.00  0.00           O  
HETATM   13  C11 UNL     1       0.755   0.254  -4.884  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.079   1.538  -2.877  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.832   2.000  -3.987  1.00  0.00           O  
HETATM   16  C13 UNL     1      -3.827   1.118  -4.501  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.664   1.747  -1.631  1.00  0.00           C  
HETATM   18  O4  UNL     1      -3.808   2.313  -1.414  1.00  0.00           O  
HETATM   19  C15 UNL     1      -4.907   2.846  -1.076  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.928   1.288  -0.499  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.801  -1.906   1.529  1.00  0.00           C  
HETATM   22  C18 UNL     1       3.480  -2.373   2.667  1.00  0.00           C  
HETATM   23  O5  UNL     1       4.457  -3.240   2.545  1.00  0.00           O  
HETATM   24  H1  UNL     1       4.415  -2.276   7.048  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.454  -0.948   6.396  1.00  0.00           H  
HETATM   26  H3  UNL     1       2.612  -2.472   6.676  1.00  0.00           H  
HETATM   27  H4  UNL     1       1.810  -0.665   5.025  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.633   0.157   3.049  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.481  -0.850  -0.503  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.393   0.495   1.482  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.746   0.035  -2.116  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.736   0.464  -4.345  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.957   0.673  -5.914  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.749  -0.882  -4.962  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.694   0.900  -5.572  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.842   1.544  -4.376  1.00  0.00           H  
HETATM   37  H14 UNL     1      -3.781   0.152  -3.964  1.00  0.00           H  
HETATM   38  H15 UNL     1      -5.751   2.913  -1.861  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.818   3.933  -0.751  1.00  0.00           H  
HETATM   40  H17 UNL     1      -5.412   2.325  -0.168  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.359   1.439   0.475  1.00  0.00           H  
HETATM   42  H19 UNL     1       3.072  -2.255   0.542  1.00  0.00           H  
HETATM   43  H20 UNL     1       5.104  -3.829   2.340  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   27
CONECT    5    6    6   28
CONECT    6    7   21
CONECT    7    8    8   29
CONECT    8    9   30
CONECT    9   10   10   20
CONECT   10   11   31
CONECT   11   12   14   14
CONECT   12   13
CONECT   13   32   33   34
CONECT   14   15   17
CONECT   15   16
CONECT   16   35   36   37
CONECT   17   18   20   20
CONECT   18   19
CONECT   19   38   39   40
CONECT   20   41
CONECT   21   22   22   42
CONECT   22   23
CONECT   23   43
END

HMDB0250413
     RDKit          3D
Combretastatin A4
 43 44  0  0  0  0  0  0  0  0999 V2000
    3.6014   -2.0695    6.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -2.4146    5.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1371   -1.9330    3.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1048   -1.0231    4.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4418   -0.5668    2.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7609   -0.9839    1.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0669   -0.5315    0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0009    0.2052    0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7128    0.6779   -0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1996    0.5062   -1.9325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8736    0.9378   -3.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3221    0.7538   -4.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7552    0.2541   -4.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0793    1.5384   -2.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316    2.0001   -3.9872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8267    1.1185   -4.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6636    1.7469   -1.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8077    2.3125   -1.4145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9070    2.8461   -1.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9278    1.2880   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8013   -1.9058    1.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4800   -2.3727    2.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4570   -3.2395    2.5454 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4149   -2.2761    7.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -0.9479    6.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117   -2.4720    6.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8104   -0.6646    5.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333    0.1570    3.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814   -0.8502   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3935    0.4951    1.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    0.0351   -2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7362    0.4643   -4.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9572    0.6731   -5.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488   -0.8818   -4.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6942    0.8996   -5.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8425    1.5444   -4.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7812    0.1522   -3.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7510    2.9132   -1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8182    3.9333   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4123    2.3249   -0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    1.4390    0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0724   -2.2548    0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1041   -3.8290    2.3401 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  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  2  0
  6 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 20  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 30  1  0
 10 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 23 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₂₀O₅

Average Molecular Weight

316.353

Monoisotopic Molecular Weight

316.131073744

IUPAC Name

2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenol

Traditional Name

combretastatin A-4

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=CC2=CC(OC)=C(OC)C(OC)=C2)C=C1O

InChI Identifier

InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3

InChI Key

HVXBOLULGPECHP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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 (HMDB: HMDB0250413)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.32	ALOGPS
logP	3.38	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.84	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.15 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	89.35 m³·mol⁻¹	ChemAxon
Polarizability	34.63 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	170.655	30932474
DeepCCS	[M-H]-	168.297	30932474
DeepCCS	[M-2H]-	202.056	30932474
DeepCCS	[M+Na]+	177.362	30932474
AllCCS	[M+H]+	177.5	32859911
AllCCS	[M+H-H2O]+	174.4	32859911
AllCCS	[M+NH4]+	180.4	32859911
AllCCS	[M+Na]+	181.2	32859911
AllCCS	[M-H]-	179.7	32859911
AllCCS	[M+Na-2H]-	179.5	32859911
AllCCS	[M+HCOO]-	179.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Combretastatin A4	COC1=CC=C(C=CC2=CC(OC)=C(OC)C(OC)=C2)C=C1O	4682.1	Standard polar	33892256
Combretastatin A4	COC1=CC=C(C=CC2=CC(OC)=C(OC)C(OC)=C2)C=C1O	2717.2	Standard non polar	33892256
Combretastatin A4	COC1=CC=C(C=CC2=CC(OC)=C(OC)C(OC)=C2)C=C1O	2830.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Combretastatin A4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-0498000000-274603e64cc381fa4f89	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Combretastatin A4 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Combretastatin A4 GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Combretastatin A4 GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - Combretastatin A4 10V, Positive-QTOF	splash10-014i-0019000000-b350b3bd4258312c0022	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Combretastatin A4 20V, Positive-QTOF	splash10-014i-0397000000-ae7e9a82ea2ae0004123	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Combretastatin A4 40V, Positive-QTOF	splash10-01bd-0590000000-76dc664bf755d1e84f10	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Combretastatin A4 10V, Negative-QTOF	splash10-014i-0009000000-23ac50f9ae12ab6825c2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Combretastatin A4 20V, Negative-QTOF	splash10-0159-0091000000-52e28ac51720aa708cc5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Combretastatin A4 40V, Negative-QTOF	splash10-0600-3591000000-6d2c93e1822e19277fa9	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

65536

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Combretastatin A4 (HMDB0250413)

MOL for HMDB0250413 (Combretastatin A4)

3D MOL for HMDB0250413 (Combretastatin A4)

3D SDF for HMDB0250413 (Combretastatin A4)

3D-SDF for HMDB0250413 (Combretastatin A4)

PDB for HMDB0250413 (Combretastatin A4)

3D PDB for HMDB0250413 (Combretastatin A4)

SMILES for HMDB0250413 (Combretastatin A4)

INCHI for HMDB0250413 (Combretastatin A4)

Structure for HMDB0250413 (Combretastatin A4)

3D Structure for HMDB0250413 (Combretastatin A4)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra