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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:05:46 UTC

Update Date

2022-03-07 02:57:00 UTC

HMDB ID

HMDB0041414

Secondary Accession Numbers

HMDB41414

Metabolite Identification

Common Name

Chloromarmin

Description

Chloromarmin belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Chloromarmin has been detected, but not quantified in, fruits. This could make chloromarmin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Chloromarmin.

Structure

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

HMDB0041414
     RDKit          3D
Chloromarmin
 47 48  0  0  0  0  0  0  0  0999 V2000
   -1.6000    2.3400   -0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0788    1.0213   -1.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2636    0.8925   -1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008    2.0041   -1.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1469    1.8113   -0.1359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1529    0.8879   -0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4043   -0.0340   -1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4492   -0.9550   -0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2328   -0.9431    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2589   -1.8550    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0457   -1.8430    1.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7523   -0.9074    2.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4808   -0.9029    3.4993 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7725   -0.0553    2.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0003   -0.0397    1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9811    0.8544    1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8882   -0.1777   -1.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6922   -0.7179   -0.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7284    0.1991    0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6523    0.5499   -0.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5803   -0.6062    1.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6067    0.3570    1.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2641   -1.7615    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5120   -1.1085    2.5008 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917    3.1844   -1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4918    2.4851    0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    2.3964   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.0827   -1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6991    2.9974   -1.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8096    2.1376   -2.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8622   -0.1028   -1.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403   -1.6738   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4384   -2.5663   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8272   -2.5673    1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7743    1.5842    1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2680   -1.0169   -1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5468    0.1009   -2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0394   -1.0658    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2328   -1.6540   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3379    1.0572    0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4601    0.1204   -1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5116    0.2862    1.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2323    1.4024    1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8328    0.1557    2.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3395   -1.7808    0.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7380   -2.6981    0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2670   -1.7100   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 16  6  1  0
 15  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
M  END


  Mrv0541 02241211082D          

 24 25  0  0  0  0            999 V2000
    3.5682   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5682    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2832    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2832    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9982   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7109   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7164   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2846    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9982   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2846    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9982    0.4111    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 21  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 19 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041414

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(CCC(O)C(C)(C)Cl)=C/COC1=CC=C2C=CC(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H23ClO4/c1-13(4-8-17(21)19(2,3)20)10-11-23-15-7-5-14-6-9-18(22)24-16(14)12-15/h5-7,9-10,12,17,21H,4,8,11H2,1-3H3/b13-10+

> <INCHI_KEY>
LJKOFXGMGDOURN-JLHYYAGUSA-N

> <FORMULA>
C19H23ClO4

> <MOLECULAR_WEIGHT>
350.837

> <EXACT_MASS>
350.128486931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.89613005391971

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-{[(2E)-7-chloro-6-hydroxy-3,7-dimethyloct-2-en-1-yl]oxy}-2H-chromen-2-one

> <ALOGPS_LOGP>
4.45

> <JCHEM_LOGP>
3.860801759666667

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.938658984014555

> <JCHEM_PKA_STRONGEST_BASIC>
-3.263030560392033

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
96.33120000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-{[(2E)-7-chloro-6-hydroxy-3,7-dimethyloct-2-en-1-yl]oxy}chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041414
     RDKit          3D
Chloromarmin
 47 48  0  0  0  0  0  0  0  0999 V2000
   -1.6000    2.3400   -0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0788    1.0213   -1.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2636    0.8925   -1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008    2.0041   -1.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1469    1.8113   -0.1359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1529    0.8879   -0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4043   -0.0340   -1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4492   -0.9550   -0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2328   -0.9431    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2589   -1.8550    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0457   -1.8430    1.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7523   -0.9074    2.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4808   -0.9029    3.4993 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7725   -0.0553    2.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0003   -0.0397    1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9811    0.8544    1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8882   -0.1777   -1.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6922   -0.7179   -0.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7284    0.1991    0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6523    0.5499   -0.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5803   -0.6062    1.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6067    0.3570    1.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2641   -1.7615    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5120   -1.1085    2.5008 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917    3.1844   -1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4918    2.4851    0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    2.3964   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.0827   -1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6991    2.9974   -1.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8096    2.1376   -2.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8622   -0.1028   -1.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403   -1.6738   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4384   -2.5663   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8272   -2.5673    1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7743    1.5842    1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2680   -1.0169   -1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5468    0.1009   -2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0394   -1.0658    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2328   -1.6540   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3379    1.0572    0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4601    0.1204   -1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5116    0.2862    1.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2323    1.4024    1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8328    0.1557    2.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3395   -1.7808    0.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7380   -2.6981    0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2670   -1.7100   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 16  6  1  0
 15  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 23 46  1  0
 23 47  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       6.661  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.329   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.994  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.659   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.659   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.994   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.329   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.661   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.995   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.995   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.330  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.327  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.005   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.337  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.669   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.333   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.666  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.998   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.330  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.669   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.666  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -7.998   1.540   0.000  0.00  0.00           C+0
HETATM   24 Cl   UNK     0      -9.330   0.767   0.000  0.00  0.00          Cl+0
CONECT    1    2   10                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    1    9   11                                                  
CONECT   11   10                                                            
CONECT   12    4   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   23   24                                             
CONECT   20   19                                                            
CONECT   21   15                                                            
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   19                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0041414
HETATM    1  C1  UNL     1      -1.600   2.340  -0.850  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.079   1.021  -1.230  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.264   0.892  -1.362  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.201   2.004  -1.141  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.147   1.811  -0.136  1.00  0.00           O  
HETATM    6  C5  UNL     1       3.153   0.888  -0.057  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.404  -0.034  -1.046  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.449  -0.955  -0.899  1.00  0.00           C  
HETATM    9  C8  UNL     1       5.233  -0.943   0.236  1.00  0.00           C  
HETATM   10  C9  UNL     1       6.259  -1.855   0.368  1.00  0.00           C  
HETATM   11  C10 UNL     1       7.046  -1.843   1.507  1.00  0.00           C  
HETATM   12  C11 UNL     1       6.752  -0.907   2.454  1.00  0.00           C  
HETATM   13  O2  UNL     1       7.481  -0.903   3.499  1.00  0.00           O  
HETATM   14  O3  UNL     1       5.772  -0.055   2.301  1.00  0.00           O  
HETATM   15  C12 UNL     1       5.000  -0.040   1.223  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.981   0.854   1.075  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.888  -0.178  -1.503  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.692  -0.718  -0.381  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.728   0.199   0.179  1.00  0.00           C  
HETATM   20  O4  UNL     1      -4.652   0.550  -0.820  1.00  0.00           O  
HETATM   21  C17 UNL     1      -4.580  -0.606   1.190  1.00  0.00           C  
HETATM   22  C18 UNL     1      -5.607   0.357   1.726  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.264  -1.761   0.513  1.00  0.00           C  
HETATM   24 CL1  UNL     1      -3.512  -1.108   2.501  1.00  0.00          CL  
HETATM   25  H1  UNL     1      -1.192   3.184  -1.459  1.00  0.00           H  
HETATM   26  H2  UNL     1      -1.492   2.485   0.232  1.00  0.00           H  
HETATM   27  H3  UNL     1      -2.708   2.396  -1.068  1.00  0.00           H  
HETATM   28  H4  UNL     1       0.608  -0.083  -1.638  1.00  0.00           H  
HETATM   29  H5  UNL     1       0.699   2.997  -1.046  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.810   2.138  -2.098  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.862  -0.103  -1.956  1.00  0.00           H  
HETATM   32  H8  UNL     1       4.640  -1.674  -1.676  1.00  0.00           H  
HETATM   33  H9  UNL     1       6.438  -2.566  -0.415  1.00  0.00           H  
HETATM   34  H10 UNL     1       7.827  -2.567   1.564  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.774   1.584   1.846  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.268  -1.017  -1.937  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.547   0.101  -2.390  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.039  -1.066   0.478  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.233  -1.654  -0.724  1.00  0.00           H  
HETATM   40  H16 UNL     1      -3.338   1.057   0.736  1.00  0.00           H  
HETATM   41  H17 UNL     1      -4.460   0.120  -1.677  1.00  0.00           H  
HETATM   42  H18 UNL     1      -6.512   0.286   1.077  1.00  0.00           H  
HETATM   43  H19 UNL     1      -5.232   1.402   1.679  1.00  0.00           H  
HETATM   44  H20 UNL     1      -5.833   0.156   2.789  1.00  0.00           H  
HETATM   45  H21 UNL     1      -6.339  -1.781   0.848  1.00  0.00           H  
HETATM   46  H22 UNL     1      -4.738  -2.698   0.813  1.00  0.00           H  
HETATM   47  H23 UNL     1      -5.267  -1.710  -0.578  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3   17
CONECT    3    4   28
CONECT    4    5   29   30
CONECT    5    6
CONECT    6    7    7   16
CONECT    7    8   31
CONECT    8    9    9   32
CONECT    9   10   15
CONECT   10   11   11   33
CONECT   11   12   34
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16   16
CONECT   16   35
CONECT   17   18   36   37
CONECT   18   19   38   39
CONECT   19   20   21   40
CONECT   20   41
CONECT   21   22   23   24
CONECT   22   42   43   44
CONECT   23   45   46   47
END

HMDB0041414
     RDKit          3D
Chloromarmin
 47 48  0  0  0  0  0  0  0  0999 V2000
   -1.6000    2.3400   -0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0788    1.0213   -1.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2636    0.8925   -1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008    2.0041   -1.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1469    1.8113   -0.1359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1529    0.8879   -0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4043   -0.0340   -1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4492   -0.9550   -0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2328   -0.9431    0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2589   -1.8550    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0457   -1.8430    1.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7523   -0.9074    2.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4808   -0.9029    3.4993 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7725   -0.0553    2.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0003   -0.0397    1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9811    0.8544    1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8882   -0.1777   -1.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6922   -0.7179   -0.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7284    0.1991    0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6523    0.5499   -0.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5803   -0.6062    1.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6067    0.3570    1.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2641   -1.7615    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5120   -1.1085    2.5008 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917    3.1844   -1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4918    2.4851    0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    2.3964   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.0827   -1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6991    2.9974   -1.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8096    2.1376   -2.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8622   -0.1028   -1.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403   -1.6738   -1.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4384   -2.5663   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8272   -2.5673    1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7743    1.5842    1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2680   -1.0169   -1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5468    0.1009   -2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0394   -1.0658    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2328   -1.6540   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3379    1.0572    0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4601    0.1204   -1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5116    0.2862    1.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2323    1.4024    1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8328    0.1557    2.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3395   -1.7808    0.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7380   -2.6981    0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2670   -1.7100   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 16  6  1  0
 15  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₃ClO₄

Average Molecular Weight

350.837

Monoisotopic Molecular Weight

350.128486931

IUPAC Name

7-{[(2E)-7-chloro-6-hydroxy-3,7-dimethyloct-2-en-1-yl]oxy}-2H-chromen-2-one

Traditional Name

7-{[(2E)-7-chloro-6-hydroxy-3,7-dimethyloct-2-en-1-yl]oxy}chromen-2-one

CAS Registry Number

169869-82-3

SMILES

C\C(CCC(O)C(C)(C)Cl)=C/COC1=CC=C2C=CC(=O)OC2=C1

InChI Identifier

InChI=1S/C19H23ClO4/c1-13(4-8-17(21)19(2,3)20)10-11-23-15-7-5-14-6-9-18(22)24-16(14)12-15/h5-7,9-10,12,17,21H,4,8,11H2,1-3H3/b13-10+

InChI Key

LJKOFXGMGDOURN-JLHYYAGUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Chlorohydrin
Halohydrin
Lactone
Secondary alcohol
Ether
Oxacycle
Organoheterocyclic compound
Organochloride
Organohalogen compound
Alkyl chloride
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organooxygen compound
Alkyl halide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041414)
Cell membrane (HMDB: HMDB0041414)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041414)

Source

Exogenous

Exogenous (HMDB: HMDB0041414)

Food

Food (HMDB: HMDB0041414)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0041414)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041414)

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	3.08 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0031 g/L	ALOGPS
logP	4.45	ALOGPS
logP	3.86	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.94	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	96.33 m³·mol⁻¹	ChemAxon
Polarizability	37.9 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]+	189.342	30932474
DeepCCS	[M-H]-	186.756	30932474
DeepCCS	[M-2H]-	221.831	30932474
DeepCCS	[M+Na]+	198.121	30932474
AllCCS	[M+H]+	181.9	32859911
AllCCS	[M+H-H2O]+	179.1	32859911
AllCCS	[M+NH4]+	184.4	32859911
AllCCS	[M+Na]+	185.2	32859911
AllCCS	[M-H]-	185.5	32859911
AllCCS	[M+Na-2H]-	185.7	32859911
AllCCS	[M+HCOO]-	186.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.4 minutes	32390414
Predicted by Siyang on May 30, 2022	17.9038 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.87 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2584.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	491.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	226.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	246.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	149.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	781.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	664.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1486.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	562.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1634.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	509.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	416.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	328.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	525.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chloromarmin	C\C(CCC(O)C(C)(C)Cl)=C/COC1=CC=C2C=CC(=O)OC2=C1	3675.3	Standard polar	33892256
Chloromarmin	C\C(CCC(O)C(C)(C)Cl)=C/COC1=CC=C2C=CC(=O)OC2=C1	2723.4	Standard non polar	33892256
Chloromarmin	C\C(CCC(O)C(C)(C)Cl)=C/COC1=CC=C2C=CC(=O)OC2=C1	2942.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chloromarmin,1TMS,isomer #1	C/C(=C\COC1=CC=C2C=CC(=O)OC2=C1)CCC(O[Si](C)(C)C)C(C)(C)Cl	2901.5	Semi standard non polar	33892256
Chloromarmin,1TBDMS,isomer #1	C/C(=C\COC1=CC=C2C=CC(=O)OC2=C1)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)Cl	3152.9	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 - Chloromarmin GC-MS (Non-derivatized) - 70eV, Positive	splash10-01vo-5593000000-bd49e401c1e78bc89814	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chloromarmin GC-MS (1 TMS) - 70eV, Positive	splash10-059l-9346100000-970c7aad84aac4ffe886	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chloromarmin 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 - Chloromarmin 10V, Positive-QTOF	splash10-0ue9-0319000000-fe72028588fb887d06ae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloromarmin 20V, Positive-QTOF	splash10-0w2i-1923000000-0ddac1db96b65e85581a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloromarmin 40V, Positive-QTOF	splash10-014i-9500000000-32e7f2416e02dfd481f7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloromarmin 10V, Negative-QTOF	splash10-0002-0309000000-d4937553c1c061cfd0bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloromarmin 20V, Negative-QTOF	splash10-03di-0913000000-ad8fbdc5a0021cb84b9d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloromarmin 40V, Negative-QTOF	splash10-02t9-1900000000-2bf0f95d3ed43124c3f0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloromarmin 10V, Negative-QTOF	splash10-0002-0209000000-db06c85eaeb4d69ba798	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloromarmin 20V, Negative-QTOF	splash10-03ea-5914000000-52a954aba0c5777cb82c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloromarmin 40V, Negative-QTOF	splash10-01q9-0900000000-514c59fa8378898e202a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloromarmin 10V, Positive-QTOF	splash10-0ue9-0109000000-7b2a2603b25ad9fcd2ce	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloromarmin 20V, Positive-QTOF	splash10-08gj-1695000000-8cf17861b7af54eed605	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloromarmin 40V, Positive-QTOF	splash10-03xr-7930000000-d9cbfcdd2aa22e22c678	2021-09-24	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

FDB021359

KNApSAcK ID

C00054288

Chemspider ID

35015177

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13965510

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1892201

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Chloromarmin (HMDB0041414)

MOL for HMDB0041414 (Chloromarmin)

3D MOL for HMDB0041414 (Chloromarmin)

3D SDF for HMDB0041414 (Chloromarmin)

3D-SDF for HMDB0041414 (Chloromarmin)

PDB for HMDB0041414 (Chloromarmin)

3D PDB for HMDB0041414 (Chloromarmin)

SMILES for HMDB0041414 (Chloromarmin)

INCHI for HMDB0041414 (Chloromarmin)

Structure for HMDB0041414 (Chloromarmin)

3D Structure for HMDB0041414 (Chloromarmin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra