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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:01 UTC

Update Date

2022-03-07 02:52:41 UTC

HMDB ID

HMDB0030787

Secondary Accession Numbers

HMDB30787

Metabolite Identification

Common Name

(R)-Marmin

Description

(R)-Marmin, also known as marmin, 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). Based on a literature review very few articles have been published on (R)-Marmin.

Structure

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

HMDB0030787
     RDKit          3D
(R)-Marmin
 48 49  0  0  0  0  0  0  0  0999 V2000
    1.4150   -2.1240    0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9054   -0.8622   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3255   -0.4556    0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678   -1.3156    1.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633   -1.7254    0.7363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927   -0.8864    0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3581    0.4654    0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4548    1.2282    0.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5098    0.6220   -0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6385    1.3486   -0.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6485    0.6430   -1.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5155   -0.7191   -1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4394   -1.3578   -2.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4532   -1.3780   -1.1724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4607   -0.7319   -0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3833   -1.5114   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5818   -0.0704   -1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968    0.6442   -0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9460   -0.0873   -0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7215   -0.7497    1.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0447    0.9648    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2347    0.1918    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3291    1.6480   -1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5814    1.8299    1.1791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5689   -2.8914    0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3199   -2.5312    0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5502   -2.1818    1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6876    0.4730   -0.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850   -0.6249    2.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4729   -2.1404    1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192    0.9343    1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4376    2.2851    0.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6502    2.4011   -0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5260    1.1506   -1.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3482   -2.5675   -0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8819   -0.7153   -1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8830    0.7356   -1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1317    1.3511   -1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    1.4420    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -0.7959   -0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2491   -0.1357    1.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6161   -0.5267    0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8638   -0.3800    1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0023    0.8902    1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0583    1.0292   -1.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3828    2.0010   -1.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7160    2.5702   -1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1081    2.6159    0.8046 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
 24 48  1  0
M  END


  Mrv0541 05061305302D          

 24 25  0  0  0  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   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
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  2  0  0  0  0
  8  4  1  0  0  0  0
  9  6  2  0  0  0  0
 11 10  1  0  0  0  0
 13  1  1  0  0  0  0
 13  4  1  0  0  0  0
 13 10  2  0  0  0  0
 14  5  1  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
 16 14  2  0  0  0  0
 17  8  1  0  0  0  0
 18  9  1  0  0  0  0
 19  2  1  0  0  0  0
 19  3  1  0  0  0  0
 19 17  1  0  0  0  0
 20 17  1  0  0  0  0
 21 18  2  0  0  0  0
 22 19  1  0  0  0  0
 23 11  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030787

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(CCC(O)C(C)(C)O)=C/COC1=CC2=C(C=CC(=O)O2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O5/c1-13(4-8-17(20)19(2,3)22)10-11-23-15-7-5-14-6-9-18(21)24-16(14)12-15/h5-7,9-10,12,17,20,22H,4,8,11H2,1-3H3/b13-10+

> <INCHI_KEY>
QYYKWTUUCOTGNS-JLHYYAGUSA-N

> <FORMULA>
C19H24O5

> <MOLECULAR_WEIGHT>
332.3909

> <EXACT_MASS>
332.162373878

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.58992408836389

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
2.506209903666667

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.3213974850486

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.84245203230343

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0892666189709015

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
93.28019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030787
     RDKit          3D
(R)-Marmin
 48 49  0  0  0  0  0  0  0  0999 V2000
    1.4150   -2.1240    0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9054   -0.8622   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3255   -0.4556    0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678   -1.3156    1.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633   -1.7254    0.7363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927   -0.8864    0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3581    0.4654    0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4548    1.2282    0.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5098    0.6220   -0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6385    1.3486   -0.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6485    0.6430   -1.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5155   -0.7191   -1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4394   -1.3578   -2.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4532   -1.3780   -1.1724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4607   -0.7319   -0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3833   -1.5114   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5818   -0.0704   -1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968    0.6442   -0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9460   -0.0873   -0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7215   -0.7497    1.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0447    0.9648    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2347    0.1918    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3291    1.6480   -1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5814    1.8299    1.1791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5689   -2.8914    0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3199   -2.5312    0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5502   -2.1818    1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6876    0.4730   -0.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850   -0.6249    2.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4729   -2.1404    1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192    0.9343    1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4376    2.2851    0.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6502    2.4011   -0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5260    1.1506   -1.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3482   -2.5675   -0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8819   -0.7153   -1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8830    0.7356   -1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1317    1.3511   -1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    1.4420    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -0.7959   -0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2491   -0.1357    1.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6161   -0.5267    0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8638   -0.3800    1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0023    0.8902    1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0583    1.0292   -1.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3828    2.0010   -1.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7160    2.5702   -1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1081    2.6159    0.8046 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
 24 48  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  14.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.208  13.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.002  10.780   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -5.128  13.090   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4    8   13                                                       
CONECT    5    7   14                                                       
CONECT    6    9   14                                                       
CONECT    7    5   15                                                       
CONECT    8    4   17                                                       
CONECT    9    6   18                                                       
CONECT   10   11   13                                                       
CONECT   11   10   23                                                       
CONECT   12   15   16                                                       
CONECT   13    1    4   10                                                  
CONECT   14    5    6   16                                                  
CONECT   15    7   12   23                                                  
CONECT   16   12   14   24                                                  
CONECT   17    8   19   20                                                  
CONECT   18    9   21   24                                                  
CONECT   19    2    3   17   22                                             
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22   19                                                            
CONECT   23   11   15                                                       
CONECT   24   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0030787
HETATM    1  C1  UNL     1       1.415  -2.124   0.518  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.905  -0.862  -0.019  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.326  -0.456   0.373  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.068  -1.316   1.321  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.263  -1.725   0.736  1.00  0.00           O  
HETATM    6  C5  UNL     1      -3.293  -0.886   0.408  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.358   0.465   0.622  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.455   1.228   0.242  1.00  0.00           C  
HETATM    9  C8  UNL     1      -5.510   0.622  -0.366  1.00  0.00           C  
HETATM   10  C9  UNL     1      -6.638   1.349  -0.768  1.00  0.00           C  
HETATM   11  C10 UNL     1      -7.648   0.643  -1.373  1.00  0.00           C  
HETATM   12  C11 UNL     1      -7.515  -0.719  -1.555  1.00  0.00           C  
HETATM   13  O2  UNL     1      -8.439  -1.358  -2.107  1.00  0.00           O  
HETATM   14  O3  UNL     1      -6.453  -1.378  -1.172  1.00  0.00           O  
HETATM   15  C12 UNL     1      -5.461  -0.732  -0.587  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.383  -1.511  -0.219  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.582  -0.070  -1.026  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.797   0.644  -0.601  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.946  -0.087  -0.038  1.00  0.00           C  
HETATM   20  O4  UNL     1       3.721  -0.750   1.136  1.00  0.00           O  
HETATM   21  C17 UNL     1       5.045   0.965   0.219  1.00  0.00           C  
HETATM   22  C18 UNL     1       6.235   0.192   0.751  1.00  0.00           C  
HETATM   23  C19 UNL     1       5.329   1.648  -1.070  1.00  0.00           C  
HETATM   24  O5  UNL     1       4.581   1.830   1.179  1.00  0.00           O  
HETATM   25  H1  UNL     1       0.569  -2.891   0.309  1.00  0.00           H  
HETATM   26  H2  UNL     1       2.320  -2.531   0.013  1.00  0.00           H  
HETATM   27  H3  UNL     1       1.550  -2.182   1.602  1.00  0.00           H  
HETATM   28  H4  UNL     1      -0.688   0.473  -0.039  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.285  -0.625   2.215  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.473  -2.140   1.743  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.519   0.934   1.137  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.438   2.285   0.440  1.00  0.00           H  
HETATM   33  H9  UNL     1      -6.650   2.401  -0.584  1.00  0.00           H  
HETATM   34  H10 UNL     1      -8.526   1.151  -1.695  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.348  -2.567  -0.393  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.882  -0.715  -1.926  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.883   0.736  -1.465  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.132   1.351  -1.440  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.533   1.442   0.201  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.317  -0.796  -0.842  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.249  -0.136   1.752  1.00  0.00           H  
HETATM   42  H18 UNL     1       6.616  -0.527   0.025  1.00  0.00           H  
HETATM   43  H19 UNL     1       5.864  -0.380   1.632  1.00  0.00           H  
HETATM   44  H20 UNL     1       7.002   0.890   1.151  1.00  0.00           H  
HETATM   45  H21 UNL     1       5.058   1.029  -1.963  1.00  0.00           H  
HETATM   46  H22 UNL     1       6.383   2.001  -1.138  1.00  0.00           H  
HETATM   47  H23 UNL     1       4.716   2.570  -1.132  1.00  0.00           H  
HETATM   48  H24 UNL     1       4.108   2.616   0.805  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
CONECT   24   48
END

HMDB0030787
     RDKit          3D
(R)-Marmin
 48 49  0  0  0  0  0  0  0  0999 V2000
    1.4150   -2.1240    0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9054   -0.8622   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3255   -0.4556    0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678   -1.3156    1.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633   -1.7254    0.7363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927   -0.8864    0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3581    0.4654    0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4548    1.2282    0.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5098    0.6220   -0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6385    1.3486   -0.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6485    0.6430   -1.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5155   -0.7191   -1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4394   -1.3578   -2.1066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4532   -1.3780   -1.1724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4607   -0.7319   -0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3833   -1.5114   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5818   -0.0704   -1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968    0.6442   -0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9460   -0.0873   -0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7215   -0.7497    1.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0447    0.9648    0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2347    0.1918    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3291    1.6480   -1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5814    1.8299    1.1791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5689   -2.8914    0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3199   -2.5312    0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5502   -2.1818    1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6876    0.4730   -0.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850   -0.6249    2.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4729   -2.1404    1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192    0.9343    1.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4376    2.2851    0.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6502    2.4011   -0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5260    1.1506   -1.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3482   -2.5675   -0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8819   -0.7153   -1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8830    0.7356   -1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1317    1.3511   -1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    1.4420    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -0.7959   -0.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2491   -0.1357    1.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6161   -0.5267    0.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8638   -0.3800    1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0023    0.8902    1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0583    1.0292   -1.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3828    2.0010   -1.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7160    2.5702   -1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1081    2.6159    0.8046 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
 24 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-(6',7'-Dihydroxygeranyloxy)coumarin	HMDB
Marmin	HMDB

Chemical Formula

C₁₉H₂₄O₅

Average Molecular Weight

332.3909

Monoisotopic Molecular Weight

332.162373878

IUPAC Name

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

Traditional Name

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

CAS Registry Number

14957-38-1

SMILES

C\C(CCC(O)C(C)(C)O)=C/COC1=CC2=C(C=CC(=O)O2)C=C1

InChI Identifier

InChI=1S/C19H24O5/c1-13(4-8-17(20)19(2,3)22)10-11-23-15-7-5-14-6-9-18(21)24-16(14)12-15/h5-7,9-10,12,17,20,22H,4,8,11H2,1-3H3/b13-10+

InChI Key

QYYKWTUUCOTGNS-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
Fatty alcohol
Alkyl aryl ether
Pyranone
Pyran
Fatty acyl
Benzenoid
Tertiary alcohol
Heteroaromatic compound
Secondary alcohol
1,2-diol
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030787)

Cellular substructure

Membrane (HMDB: HMDB0030787)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030787)

Source

Endogenous

Endogenous (HMDB: HMDB0030787)

Plant

Plant (HMDB: HMDB0030787)

Exogenous

Food

Food (HMDB: HMDB0030787)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	123 - 124 °C	Not Available
Boiling Point	531.90 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	16.23 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.450 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	3.1	ALOGPS
logP	2.51	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	93.28 m³·mol⁻¹	ChemAxon
Polarizability	36.59 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
DarkChem	[M+H]+	180.299	31661259
DarkChem	[M-H]-	178.155	31661259
DeepCCS	[M+H]+	191.572	30932474
DeepCCS	[M-H]-	188.241	30932474
DeepCCS	[M-2H]-	224.097	30932474
DeepCCS	[M+Na]+	200.388	30932474
AllCCS	[M+H]+	180.5	32859911
AllCCS	[M+H-H2O]+	177.6	32859911
AllCCS	[M+NH4]+	183.2	32859911
AllCCS	[M+Na]+	184.0	32859911
AllCCS	[M-H]-	183.5	32859911
AllCCS	[M+Na-2H]-	183.8	32859911
AllCCS	[M+HCOO]-	184.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Marmin	C\C(CCC(O)C(C)(C)O)=C/COC1=CC2=C(C=CC(=O)O2)C=C1	3808.3	Standard polar	33892256
(R)-Marmin	C\C(CCC(O)C(C)(C)O)=C/COC1=CC2=C(C=CC(=O)O2)C=C1	2757.2	Standard non polar	33892256
(R)-Marmin	C\C(CCC(O)C(C)(C)O)=C/COC1=CC2=C(C=CC(=O)O2)C=C1	2962.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Marmin,1TMS,isomer #1	C/C(=C\COC1=CC=C2C=CC(=O)OC2=C1)CCC(O[Si](C)(C)C)C(C)(C)O	2899.8	Semi standard non polar	33892256
(R)-Marmin,1TMS,isomer #2	C/C(=C\COC1=CC=C2C=CC(=O)OC2=C1)CCC(O)C(C)(C)O[Si](C)(C)C	2929.2	Semi standard non polar	33892256
(R)-Marmin,2TMS,isomer #1	C/C(=C\COC1=CC=C2C=CC(=O)OC2=C1)CCC(O[Si](C)(C)C)C(C)(C)O[Si](C)(C)C	2905.0	Semi standard non polar	33892256
(R)-Marmin,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)O	3137.3	Semi standard non polar	33892256
(R)-Marmin,1TBDMS,isomer #2	C/C(=C\COC1=CC=C2C=CC(=O)OC2=C1)CCC(O)C(C)(C)O[Si](C)(C)C(C)(C)C	3170.9	Semi standard non polar	33892256
(R)-Marmin,2TBDMS,isomer #1	C/C(=C\COC1=CC=C2C=CC(=O)OC2=C1)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)O[Si](C)(C)C(C)(C)C	3369.0	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 - (R)-Marmin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9143000000-b5ff0db4041e7dc062eb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Marmin GC-MS (2 TMS) - 70eV, Positive	splash10-01q9-7945800000-8c9e650383310252c022	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Marmin 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 - (R)-Marmin 10V, Negative-QTOF	splash10-01q9-0339000000-749a91054b580eab2a7f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Marmin 20V, Negative-QTOF	splash10-03di-0922000000-2f3a91d3a9f1feaafea2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Marmin 40V, Negative-QTOF	splash10-014i-2900000000-f84d9eca03ab7d47cc7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Marmin 10V, Negative-QTOF	splash10-03e9-0908000000-8caa6681bef0b936a33b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Marmin 20V, Negative-QTOF	splash10-03di-2910000000-0423cce82b9ab500649f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Marmin 40V, Negative-QTOF	splash10-0159-0900000000-33d87450be29b1aedac5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Marmin 10V, Positive-QTOF	splash10-00lr-0449000000-8f29fd82e4fbc34a65b0	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Marmin 20V, Positive-QTOF	splash10-0ho4-4953000000-cbdfa7bea484157cac74	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Marmin 40V, Positive-QTOF	splash10-029i-9510000000-10ae74648a914da7ce39	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Marmin 10V, Positive-QTOF	splash10-00kb-0169000000-be0c48ffd91e02a405b3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Marmin 20V, Positive-QTOF	splash10-01ot-2791000000-6baf219959ed30ec432c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Marmin 40V, Positive-QTOF	splash10-03yi-9720000000-66bddcd59fad62417f43	2021-09-22	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

FDB002724

KNApSAcK ID

C00037483

Chemspider ID

4764935

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5964600

PDB ID

Not Available

ChEBI ID

172558

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1637201

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 (R)-Marmin (HMDB0030787)

MOL for HMDB0030787 ((R)-Marmin)

3D MOL for HMDB0030787 ((R)-Marmin)

3D SDF for HMDB0030787 ((R)-Marmin)

3D-SDF for HMDB0030787 ((R)-Marmin)

PDB for HMDB0030787 ((R)-Marmin)

3D PDB for HMDB0030787 ((R)-Marmin)

SMILES for HMDB0030787 ((R)-Marmin)

INCHI for HMDB0030787 ((R)-Marmin)

Structure for HMDB0030787 ((R)-Marmin)

3D Structure for HMDB0030787 ((R)-Marmin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra