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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:25:14 UTC

Update Date

2021-09-26 23:06:58 UTC

HMDB ID

HMDB0253622

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isocombretastatin A4

Description

Isocombretastatin A4, also known as CA4DP or CRC-98-09, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Based on a literature review very few articles have been published on Isocombretastatin A4. This compound has been identified in human blood as reported by (PMID: 31557052 ). Isocombretastatin a4 is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isocombretastatin 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

HMDB0253622
     RDKit          3D
Isocombretastatin A4
 43 44  0  0  0  0  0  0  0  0999 V2000
    0.2762   -2.6227    1.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3876   -1.5010    0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6898   -1.0647    0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8368   -0.2908   -0.9994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0931    0.1492   -1.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406   -0.1702   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4836    0.2799   -1.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5637    1.0642   -2.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1059   -0.9442    0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403   -1.2856    1.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -1.3774    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822   -0.7017    0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7242    0.6743    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727    1.3756   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8261    2.7207   -0.4263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6804    3.5223   -0.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0799    0.7178   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2049    1.4718   -0.6046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9181    2.0182    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1829   -0.6504   -0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946   -1.3072   -0.1824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5635   -2.6784    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262   -1.3387    0.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1598   -3.2032    1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530   -3.0276    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9827    0.0005   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.7540   -2.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0133    2.0350   -2.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6570    1.2467   -2.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576    0.5507   -3.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2176   -1.8451    1.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -1.9849    1.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2036    1.2238    0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571    3.5048    0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9774    4.5768   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0457    3.2737   -1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2633    2.8056    0.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8947    2.4500    0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0115    1.2254    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2281   -3.3115   -0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9662   -2.9743    0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6166   -2.9474    0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869   -2.4138    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
  9 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 11  3  1  0
 23 12  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
M  END

  Mrv1652309112114252D          

 23 24  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    2.8579   -4.1250    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
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    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   -3.7125    0.0000 O   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
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
  4 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253622

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C(=C)C1=CC(O)=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O5/c1-11(12-6-7-15(20-2)14(19)8-12)13-9-16(21-3)18(23-5)17(10-13)22-4/h6-10,19H,1H2,2-5H3

> <INCHI_KEY>
CNGKIRSNRQSORA-UHFFFAOYSA-N

> <FORMULA>
C18H20O5

> <MOLECULAR_WEIGHT>
316.353

> <EXACT_MASS>
316.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.954445325488976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-5-[1-(3,4,5-trimethoxyphenyl)ethenyl]phenol

> <ALOGPS_LOGP>
3.30

> <JCHEM_LOGP>
3.2088960773333337

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.772939408716846

> <JCHEM_PKA_STRONGEST_BASIC>
-4.314062719132363

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
97.1307

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxy-5-[1-(3,4,5-trimethoxyphenyl)ethenyl]phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253622
     RDKit          3D
Isocombretastatin A4
 43 44  0  0  0  0  0  0  0  0999 V2000
    0.2762   -2.6227    1.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3876   -1.5010    0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6898   -1.0647    0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8368   -0.2908   -0.9994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0931    0.1492   -1.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406   -0.1702   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4836    0.2799   -1.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5637    1.0642   -2.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1059   -0.9442    0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403   -1.2856    1.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -1.3774    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822   -0.7017    0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7242    0.6743    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727    1.3756   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8261    2.7207   -0.4263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6804    3.5223   -0.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0799    0.7178   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2049    1.4718   -0.6046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9181    2.0182    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1829   -0.6504   -0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946   -1.3072   -0.1824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5635   -2.6784    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262   -1.3387    0.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1598   -3.2032    1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530   -3.0276    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9827    0.0005   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.7540   -2.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0133    2.0350   -2.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6570    1.2467   -2.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576    0.5507   -3.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2176   -1.8451    1.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -1.9849    1.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2036    1.2238    0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571    3.5048    0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9774    4.5768   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0457    3.2737   -1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2633    2.8056    0.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8947    2.4500    0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0115    1.2254    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2281   -3.3115   -0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9662   -2.9743    0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6166   -2.9474    0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869   -2.4138    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
  9 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 11  3  1  0
 23 12  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   14   20                                                       
CONECT   20   19                                                            
CONECT   21   13   22                                                       
CONECT   22   21                                                            
CONECT   23    4                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0253622
HETATM    1  C1  UNL     1       0.276  -2.623   1.263  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.388  -1.501   0.588  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.690  -1.065   0.131  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.837  -0.291  -0.999  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.093   0.149  -1.422  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.241  -0.170  -0.730  1.00  0.00           C  
HETATM    7  O1  UNL     1       5.484   0.280  -1.170  1.00  0.00           O  
HETATM    8  C7  UNL     1       5.564   1.064  -2.326  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.106  -0.944   0.402  1.00  0.00           C  
HETATM   10  O2  UNL     1       5.240  -1.286   1.123  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.864  -1.377   0.817  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.782  -0.702   0.297  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.724   0.674   0.083  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.873   1.376  -0.215  1.00  0.00           C  
HETATM   15  O3  UNL     1      -1.826   2.721  -0.426  1.00  0.00           O  
HETATM   16  C13 UNL     1      -0.680   3.522  -0.373  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.080   0.718  -0.301  1.00  0.00           C  
HETATM   18  O4  UNL     1      -4.205   1.472  -0.605  1.00  0.00           O  
HETATM   19  C15 UNL     1      -4.918   2.018   0.493  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.183  -0.650  -0.095  1.00  0.00           C  
HETATM   21  O5  UNL     1      -4.395  -1.307  -0.182  1.00  0.00           O  
HETATM   22  C17 UNL     1      -4.564  -2.678   0.014  1.00  0.00           C  
HETATM   23  C18 UNL     1      -2.026  -1.339   0.202  1.00  0.00           C  
HETATM   24  H1  UNL     1       1.160  -3.203   1.467  1.00  0.00           H  
HETATM   25  H2  UNL     1      -0.653  -3.028   1.647  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.983   0.001  -1.628  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.150   0.754  -2.315  1.00  0.00           H  
HETATM   28  H5  UNL     1       5.013   2.035  -2.230  1.00  0.00           H  
HETATM   29  H6  UNL     1       6.657   1.247  -2.515  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.158   0.551  -3.220  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.218  -1.845   1.955  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.742  -1.985   1.708  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.204   1.224   0.161  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.157   3.505   0.596  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.977   4.577  -0.552  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.046   3.274  -1.201  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.263   2.806   0.941  1.00  0.00           H  
HETATM   38  H15 UNL     1      -5.895   2.450   0.189  1.00  0.00           H  
HETATM   39  H16 UNL     1      -5.012   1.225   1.245  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.228  -3.311  -0.819  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.966  -2.974   0.918  1.00  0.00           H  
HETATM   42  H19 UNL     1      -5.617  -2.947   0.246  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.087  -2.414   0.365  1.00  0.00           H  
CONECT    1    2    2   24   25
CONECT    2    3   12
CONECT    3    4    4   11
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7    9
CONECT    7    8
CONECT    8   28   29   30
CONECT    9   10   11   11
CONECT   10   31
CONECT   11   32
CONECT   12   13   13   23
CONECT   13   14   33
CONECT   14   15   17   17
CONECT   15   16
CONECT   16   34   35   36
CONECT   17   18   20
CONECT   18   19
CONECT   19   37   38   39
CONECT   20   21   23   23
CONECT   21   22
CONECT   22   40   41   42
CONECT   23   43
END

HMDB0253622
     RDKit          3D
Isocombretastatin A4
 43 44  0  0  0  0  0  0  0  0999 V2000
    0.2762   -2.6227    1.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3876   -1.5010    0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6898   -1.0647    0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8368   -0.2908   -0.9994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0931    0.1492   -1.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406   -0.1702   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4836    0.2799   -1.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5637    1.0642   -2.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1059   -0.9442    0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403   -1.2856    1.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -1.3774    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822   -0.7017    0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7242    0.6743    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727    1.3756   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8261    2.7207   -0.4263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6804    3.5223   -0.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0799    0.7178   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2049    1.4718   -0.6046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9181    2.0182    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1829   -0.6504   -0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946   -1.3072   -0.1824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5635   -2.6784    0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262   -1.3387    0.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1598   -3.2032    1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530   -3.0276    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9827    0.0005   -1.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    0.7540   -2.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0133    2.0350   -2.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6570    1.2467   -2.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576    0.5507   -3.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2176   -1.8451    1.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -1.9849    1.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2036    1.2238    0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571    3.5048    0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9774    4.5768   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0457    3.2737   -1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2633    2.8056    0.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8947    2.4500    0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0115    1.2254    1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2281   -3.3115   -0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9662   -2.9743    0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6166   -2.9474    0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869   -2.4138    0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
  9 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 11  3  1  0
 23 12  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methoxy-5-((Z)-2-(3,4,5-trimethoxyphenyl)vinyl)phenyl dihydrogen phosphate	HMDB
3,4,5-Trimethoxy-3'-hydroxy-4'-methoxystilbene	HMDB
Isocombretastatin a-4	HMDB
Combretastatin a-4	HMDB
Combretastatin a-4 disodium phosphate	HMDB
Combretastatin a4	HMDB
Combretastatin a4 phosphate	HMDB
Phenol, 2-methoxy-5-((Z)-2-(3,4,5-trimethoxyphenyl)ethenyl)-, dihydrogen phosphate	HMDB
CA4dp	HMDB
CRC-98-09	HMDB
Fosbretabulin	HMDB
1-(3,4,5-Trimethoxyphenyl)-2-(3'-hydroxy-4'-methoxyphenyl)ethene	HMDB
CRC 87-09	HMDB
Deoxycombretastatin a-4	HMDB
Phenol, 2-methoxy-5-((1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl)-,1-(dihydrogen phosphate)	HMDB

Chemical Formula

C₁₈H₂₀O₅

Average Molecular Weight

316.353

Monoisotopic Molecular Weight

316.131073744

IUPAC Name

2-methoxy-5-[1-(3,4,5-trimethoxyphenyl)ethenyl]phenol

Traditional Name

2-methoxy-5-[1-(3,4,5-trimethoxyphenyl)ethenyl]phenol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C(=C)C1=CC(O)=C(OC)C=C1

InChI Identifier

InChI=1S/C18H20O5/c1-11(12-6-7-15(20-2)14(19)8-12)13-9-16(21-3)18(23-5)17(10-13)22-4/h6-10,19H,1H2,2-5H3

InChI Key

CNGKIRSNRQSORA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
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 (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.3	ALOGPS
logP	3.21	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.77	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	97.13 m³·mol⁻¹	ChemAxon
Polarizability	33.95 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]+	178.78	30932474
DeepCCS	[M-H]-	176.422	30932474
DeepCCS	[M-2H]-	210.24	30932474
DeepCCS	[M+Na]+	185.466	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isocombretastatin A4	COC1=CC(=CC(OC)=C1OC)C(=C)C1=CC(O)=C(OC)C=C1	4212.2	Standard polar	33892256
Isocombretastatin A4	COC1=CC(=CC(OC)=C1OC)C(=C)C1=CC(O)=C(OC)C=C1	2609.3	Standard non polar	33892256
Isocombretastatin A4	COC1=CC(=CC(OC)=C1OC)C(=C)C1=CC(O)=C(OC)C=C1	2535.8	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 - Isocombretastatin A4 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-0797000000-a9104e8405fb973aa7ee	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocombretastatin A4 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocombretastatin A4 GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocombretastatin A4 GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Isocombretastatin A4 10V, Positive-QTOF	splash10-014i-0119000000-6a6f35e0744de33aa03c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocombretastatin A4 20V, Positive-QTOF	splash10-014i-0669000000-54dbae9f5145e1a9b2a9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocombretastatin A4 40V, Positive-QTOF	splash10-00bc-3790000000-4a25aaec712067ac1e35	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocombretastatin A4 10V, Negative-QTOF	splash10-014i-0009000000-23ac50f9ae12ab6825c2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocombretastatin A4 20V, Negative-QTOF	splash10-014i-0095000000-02af21d6d84894509fec	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocombretastatin A4 40V, Negative-QTOF	splash10-01c0-0690000000-e6234b25e29eff58aee4	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

24709355

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24996163

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 Isocombretastatin A4 (HMDB0253622)

MOL for HMDB0253622 (Isocombretastatin A4)

3D MOL for HMDB0253622 (Isocombretastatin A4)

3D SDF for HMDB0253622 (Isocombretastatin A4)

3D-SDF for HMDB0253622 (Isocombretastatin A4)

PDB for HMDB0253622 (Isocombretastatin A4)

3D PDB for HMDB0253622 (Isocombretastatin A4)

SMILES for HMDB0253622 (Isocombretastatin A4)

INCHI for HMDB0253622 (Isocombretastatin A4)

Structure for HMDB0253622 (Isocombretastatin A4)

3D Structure for HMDB0253622 (Isocombretastatin A4)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra