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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:04:25 UTC

Update Date

2022-03-07 02:54:02 UTC

HMDB ID

HMDB0034269

Secondary Accession Numbers

HMDB34269

Metabolite Identification

Common Name

Mammeisin

Description

Mammeisin belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone. Thus, mammeisin is considered to be a flavonoid. Mammeisin has been detected, but not quantified in, fruits. This could make mammeisin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Mammeisin.

Structure

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


  Mrv0541 05061307412D          

 30 32  0  0  0  0            999 V2000
    2.8579   -1.6500    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
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    0.0000    2.4750    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
   -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
    2.1434    2.0625    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
    1.4289    2.4750    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    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 11 10  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14 10  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15 12  1  0  0  0  0
 16  8  2  0  0  0  0
 16  9  1  0  0  0  0
 17 11  1  0  0  0  0
 18 13  2  0  0  0  0
 18 16  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
 23 17  1  0  0  0  0
 23 22  2  0  0  0  0
 24 21  2  0  0  0  0
 24 22  1  0  0  0  0
 25 17  2  0  0  0  0
 25 21  1  0  0  0  0
 26 19  2  0  0  0  0
 27 20  2  0  0  0  0
 28 23  1  0  0  0  0
 29 24  1  0  0  0  0
 30 20  1  0  0  0  0
 30 25  1  0  0  0  0
M  END

HMDB0034269
     RDKit          3D
Mammeisin
 56 58  0  0  0  0  0  0  0  0999 V2000
    3.9389   -3.6119    2.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797   -3.0755    1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7914   -2.6748    0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364   -2.9573    0.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1158   -2.4217   -0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298   -1.2291   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1169   -1.3737   -0.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208   -2.6631   -0.1499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9933   -0.2948   -0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4036   -0.4959    0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2342    0.4332    0.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9195   -1.8961    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4279   -1.8671    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8326   -1.0831    1.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0957   -1.4091   -0.8208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4926    0.9824   -0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981    2.1404   -0.3495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8789    1.1086   -0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    2.3841   -0.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5541    3.5821   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4013    4.2093    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3766    5.3620    0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150    5.9030   -0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8641    5.2762   -1.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815    4.1184   -1.8410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453    2.5058   -1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5465    1.4033   -1.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092    1.5257   -1.3419 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0326    0.2165   -0.9547 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7356    0.0422   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5082   -4.6438    2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0325   -3.7009    2.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4464   -3.0155    3.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7731   -1.5874    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664   -2.9693    0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6971   -3.2144   -0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6367   -3.2575    1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450   -3.2084   -1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0467   -2.1146   -1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0905   -3.5040   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7945   -2.4090   -0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4876   -2.4074    1.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7156   -2.9492    0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4368   -1.7339    2.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9268   -0.7734    2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4660   -0.2041    1.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0561   -1.9432   -0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1955   -0.3267   -0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4336   -1.7492   -1.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1520    2.2535   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8865    3.8224    1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4834    5.8424    1.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331    6.8130   -0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3721    5.7127   -2.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    3.6459   -2.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1640    3.4824   -1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 19 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30  6  1  0
 30 18  2  0
 25 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
 26 56  1  0
M  END


  Mrv0541 05061307412D          

 30 32  0  0  0  0            999 V2000
    2.8579   -1.6500    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
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    0.0000    2.4750    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
   -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
    2.1434    2.0625    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
    1.4289    2.4750    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    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 11 10  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14 10  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15 12  1  0  0  0  0
 16  8  2  0  0  0  0
 16  9  1  0  0  0  0
 17 11  1  0  0  0  0
 18 13  2  0  0  0  0
 18 16  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
 23 17  1  0  0  0  0
 23 22  2  0  0  0  0
 24 21  2  0  0  0  0
 24 22  1  0  0  0  0
 25 17  2  0  0  0  0
 25 21  1  0  0  0  0
 26 19  2  0  0  0  0
 27 20  2  0  0  0  0
 28 23  1  0  0  0  0
 29 24  1  0  0  0  0
 30 20  1  0  0  0  0
 30 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034269

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O5/c1-14(2)10-11-17-23(28)22(19(26)12-15(3)4)24(29)21-18(13-20(27)30-25(17)21)16-8-6-5-7-9-16/h5-10,13,15,28-29H,11-12H2,1-4H3

> <INCHI_KEY>
JIFOADIANOIMSK-UHFFFAOYSA-N

> <FORMULA>
C25H26O5

> <MOLECULAR_WEIGHT>
406.4709

> <EXACT_MASS>
406.178023942

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
44.54126392452827

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-6-(3-methylbutanoyl)-4-phenyl-2H-chromen-2-one

> <ALOGPS_LOGP>
4.82

> <JCHEM_LOGP>
6.627765676

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.137237502605604

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.964746042053839

> <JCHEM_PKA_STRONGEST_BASIC>
-5.203973381508953

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
127.48519999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.97e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mammeisin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034269
     RDKit          3D
Mammeisin
 56 58  0  0  0  0  0  0  0  0999 V2000
    3.9389   -3.6119    2.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797   -3.0755    1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7914   -2.6748    0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364   -2.9573    0.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1158   -2.4217   -0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298   -1.2291   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1169   -1.3737   -0.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208   -2.6631   -0.1499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9933   -0.2948   -0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4036   -0.4959    0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2342    0.4332    0.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9195   -1.8961    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4279   -1.8671    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8326   -1.0831    1.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0957   -1.4091   -0.8208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4926    0.9824   -0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981    2.1404   -0.3495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8789    1.1086   -0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    2.3841   -0.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5541    3.5821   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4013    4.2093    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3766    5.3620    0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150    5.9030   -0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8641    5.2762   -1.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815    4.1184   -1.8410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453    2.5058   -1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5465    1.4033   -1.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092    1.5257   -1.3419 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0326    0.2165   -0.9547 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7356    0.0422   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5082   -4.6438    2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0325   -3.7009    2.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4464   -3.0155    3.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7731   -1.5874    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664   -2.9693    0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6971   -3.2144   -0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6367   -3.2575    1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450   -3.2084   -1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0467   -2.1146   -1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0905   -3.5040   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7945   -2.4090   -0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4876   -2.4074    1.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7156   -2.9492    0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4368   -1.7339    2.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9268   -0.7734    2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4660   -0.2041    1.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0561   -1.9432   -0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1955   -0.3267   -0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4336   -1.7492   -1.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1520    2.2535   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8865    3.8224    1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4834    5.8424    1.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331    6.8130   -0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3721    5.7127   -2.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    3.6459   -2.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1640    3.4824   -1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 19 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30  6  1  0
 30 18  2  0
 25 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
 26 56  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       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   16                                                       
CONECT    9    7   16                                                       
CONECT   10   11   14                                                       
CONECT   11   10   17                                                       
CONECT   12   15   19                                                       
CONECT   13   18   20                                                       
CONECT   14    1    2   10                                                  
CONECT   15    3    4   12                                                  
CONECT   16    8    9   18                                                  
CONECT   17   11   23   25                                                  
CONECT   18   13   16   21                                                  
CONECT   19   12   22   26                                                  
CONECT   20   13   27   30                                                  
CONECT   21   18   24   25                                                  
CONECT   22   19   23   24                                                  
CONECT   23   17   22   28                                                  
CONECT   24   21   22   29                                                  
CONECT   25   17   21   30                                                  
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28   23                                                            
CONECT   29   24                                                            
CONECT   30   20   25                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0034269
HETATM    1  C1  UNL     1       3.939  -3.612   2.519  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.680  -3.076   1.163  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.791  -2.675   0.268  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.436  -2.957   0.739  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.116  -2.422  -0.620  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.230  -1.229  -0.554  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.117  -1.374  -0.314  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.621  -2.663  -0.150  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.993  -0.295  -0.232  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.404  -0.496   0.027  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.234   0.433   0.108  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.919  -1.896   0.213  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.428  -1.867   0.441  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.833  -1.083   1.642  1.00  0.00           C  
HETATM   15  C13 UNL     1      -5.096  -1.409  -0.821  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.493   0.982  -0.398  1.00  0.00           C  
HETATM   17  O3  UNL     1      -1.198   2.140  -0.349  1.00  0.00           O  
HETATM   18  C15 UNL     1       0.879   1.109  -0.641  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.396   2.384  -0.811  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.554   3.582  -0.747  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.401   4.209   0.464  1.00  0.00           C  
HETATM   22  C19 UNL     1      -0.377   5.362   0.594  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.015   5.903  -0.497  1.00  0.00           C  
HETATM   24  C21 UNL     1      -0.864   5.276  -1.715  1.00  0.00           C  
HETATM   25  C22 UNL     1      -0.082   4.118  -1.841  1.00  0.00           C  
HETATM   26  C23 UNL     1       2.745   2.506  -1.050  1.00  0.00           C  
HETATM   27  C24 UNL     1       3.547   1.403  -1.118  1.00  0.00           C  
HETATM   28  O4  UNL     1       4.809   1.526  -1.342  1.00  0.00           O  
HETATM   29  O5  UNL     1       3.033   0.216  -0.955  1.00  0.00           O  
HETATM   30  C25 UNL     1       1.736   0.042  -0.721  1.00  0.00           C  
HETATM   31  H1  UNL     1       3.508  -4.644   2.621  1.00  0.00           H  
HETATM   32  H2  UNL     1       5.033  -3.701   2.715  1.00  0.00           H  
HETATM   33  H3  UNL     1       3.446  -3.016   3.316  1.00  0.00           H  
HETATM   34  H4  UNL     1       4.773  -1.587   0.133  1.00  0.00           H  
HETATM   35  H5  UNL     1       5.766  -2.969   0.740  1.00  0.00           H  
HETATM   36  H6  UNL     1       4.697  -3.214  -0.705  1.00  0.00           H  
HETATM   37  H7  UNL     1       1.637  -3.258   1.403  1.00  0.00           H  
HETATM   38  H8  UNL     1       1.645  -3.208  -1.255  1.00  0.00           H  
HETATM   39  H9  UNL     1       3.047  -2.115  -1.133  1.00  0.00           H  
HETATM   40  H10 UNL     1      -0.090  -3.504  -0.199  1.00  0.00           H  
HETATM   41  H11 UNL     1      -2.794  -2.409  -0.756  1.00  0.00           H  
HETATM   42  H12 UNL     1      -2.488  -2.407   1.078  1.00  0.00           H  
HETATM   43  H13 UNL     1      -4.716  -2.949   0.576  1.00  0.00           H  
HETATM   44  H14 UNL     1      -5.437  -1.734   2.336  1.00  0.00           H  
HETATM   45  H15 UNL     1      -3.927  -0.773   2.195  1.00  0.00           H  
HETATM   46  H16 UNL     1      -5.466  -0.204   1.408  1.00  0.00           H  
HETATM   47  H17 UNL     1      -6.056  -1.943  -0.984  1.00  0.00           H  
HETATM   48  H18 UNL     1      -5.196  -0.327  -0.905  1.00  0.00           H  
HETATM   49  H19 UNL     1      -4.434  -1.749  -1.669  1.00  0.00           H  
HETATM   50  H20 UNL     1      -2.152   2.254  -0.192  1.00  0.00           H  
HETATM   51  H21 UNL     1       0.887   3.822   1.366  1.00  0.00           H  
HETATM   52  H22 UNL     1      -0.483   5.842   1.564  1.00  0.00           H  
HETATM   53  H23 UNL     1      -1.633   6.813  -0.407  1.00  0.00           H  
HETATM   54  H24 UNL     1      -1.372   5.713  -2.565  1.00  0.00           H  
HETATM   55  H25 UNL     1       0.022   3.646  -2.802  1.00  0.00           H  
HETATM   56  H26 UNL     1       3.164   3.482  -1.183  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    4    4
CONECT    3   34   35   36
CONECT    4    5   37
CONECT    5    6   38   39
CONECT    6    7    7   30
CONECT    7    8    9
CONECT    8   40
CONECT    9   10   16   16
CONECT   10   11   11   12
CONECT   12   13   41   42
CONECT   13   14   15   43
CONECT   14   44   45   46
CONECT   15   47   48   49
CONECT   16   17   18
CONECT   17   50
CONECT   18   19   30   30
CONECT   19   20   26   26
CONECT   20   21   21   25
CONECT   21   22   51
CONECT   22   23   23   52
CONECT   23   24   53
CONECT   24   25   25   54
CONECT   25   55
CONECT   26   27   56
CONECT   27   28   28   29
CONECT   29   30
END

HMDB0034269
     RDKit          3D
Mammeisin
 56 58  0  0  0  0  0  0  0  0999 V2000
    3.9389   -3.6119    2.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797   -3.0755    1.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7914   -2.6748    0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364   -2.9573    0.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1158   -2.4217   -0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298   -1.2291   -0.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1169   -1.3737   -0.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208   -2.6631   -0.1499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9933   -0.2948   -0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4036   -0.4959    0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2342    0.4332    0.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9195   -1.8961    0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4279   -1.8671    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8326   -1.0831    1.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0957   -1.4091   -0.8208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4926    0.9824   -0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981    2.1404   -0.3495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8789    1.1086   -0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3962    2.3841   -0.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5541    3.5821   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4013    4.2093    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3766    5.3620    0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150    5.9030   -0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8641    5.2762   -1.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815    4.1184   -1.8410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453    2.5058   -1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5465    1.4033   -1.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092    1.5257   -1.3419 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0326    0.2165   -0.9547 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7356    0.0422   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5082   -4.6438    2.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0325   -3.7009    2.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4464   -3.0155    3.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7731   -1.5874    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664   -2.9693    0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6971   -3.2144   -0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6367   -3.2575    1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450   -3.2084   -1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0467   -2.1146   -1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0905   -3.5040   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7945   -2.4090   -0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4876   -2.4074    1.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7156   -2.9492    0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4368   -1.7339    2.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9268   -0.7734    2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4660   -0.2041    1.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0561   -1.9432   -0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1955   -0.3267   -0.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4336   -1.7492   -1.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1520    2.2535   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8865    3.8224    1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4834    5.8424    1.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331    6.8130   -0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3721    5.7127   -2.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    3.6459   -2.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1640    3.4824   -1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 19 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30  6  1  0
 30 18  2  0
 25 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  0
 26 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,7-Dihydroxy-8-(3-methyl-2-butenyl)-6-(3-methyl-1-oxobutyl)-4-phenyl-2H-1-benzopyran-2-one, 9ci	HMDB
5,7-Dihydroxy-8-(3-methyl-2-butenyl)-6-(3-methylbutyryl)-4-phenylcoumarin	HMDB
5,7-Dihydroxy-8-isopentenyl-6-isovaleroyl-4-phenylcoumarin	HMDB
Mammea a/aa	HMDB

Chemical Formula

C₂₅H₂₆O₅

Average Molecular Weight

406.4709

Monoisotopic Molecular Weight

406.178023942

IUPAC Name

5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-6-(3-methylbutanoyl)-4-phenyl-2H-chromen-2-one

Traditional Name

mammeisin

CAS Registry Number

18483-64-2

SMILES

CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O

InChI Identifier

InChI=1S/C25H26O5/c1-14(2)10-11-17-23(28)22(19(26)12-15(3)4)24(29)21-18(13-20(27)30-25(17)21)16-8-6-5-7-9-16/h5-10,13,15,28-29H,11-12H2,1-4H3

InChI Key

JIFOADIANOIMSK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Prenylated neoflavonoids

Direct Parent

Prenylated neoflavonoids

Alternative Parents

Substituents

Prenylated neoflavonoid
4-phenylcoumarin
7-hydroxycoumarin
Hydroxycoumarin
Butyrophenone
Coumarin
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Lactone
Ketone
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

neoflavonoid (CHEBI:69990 )
Neoflavonoids (C09275 )
Neoflavonoids (LMPK12100002 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034269)
Cell membrane (HMDB: HMDB0034269)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034269)

Source

Exogenous

Exogenous (HMDB: HMDB0034269)

Food

Food (HMDB: HMDB0034269)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0034269)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034269)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	98 - 109 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.03 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	0.005 g/L	ALOGPS
logP	4.82	ALOGPS
logP	6.63	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	7.96	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	127.49 m³·mol⁻¹	ChemAxon
Polarizability	44.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	196.96	31661259
DarkChem	[M-H]-	196.571	31661259
DeepCCS	[M+H]+	206.146	30932474
DeepCCS	[M-H]-	203.788	30932474
DeepCCS	[M-2H]-	237.704	30932474
DeepCCS	[M+Na]+	212.969	30932474
AllCCS	[M+H]+	198.2	32859911
AllCCS	[M+H-H2O]+	195.6	32859911
AllCCS	[M+NH4]+	200.7	32859911
AllCCS	[M+Na]+	201.4	32859911
AllCCS	[M-H]-	202.4	32859911
AllCCS	[M+Na-2H]-	202.4	32859911
AllCCS	[M+HCOO]-	202.5	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.	10.45 minutes	32390414
Predicted by Siyang on May 30, 2022	23.4844 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.84 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	32.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3945.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	722.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	300.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	380.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	451.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	963.4 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	1185.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1998.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	821.4 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	2070.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	654.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	655.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	439.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	383.9 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	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mammeisin	CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O	4159.1	Standard polar	33892256
Mammeisin	CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O	2830.4	Standard non polar	33892256
Mammeisin	CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O	3316.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mammeisin,1TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C(O)C2=C1OC(=O)C=C2C1=CC=CC=C1	3201.2	Semi standard non polar	33892256
Mammeisin,1TMS,isomer #2	CC(C)=CCC1=C(O)C(C(=O)CC(C)C)=C(O[Si](C)(C)C)C2=C1OC(=O)C=C2C1=CC=CC=C1	3208.4	Semi standard non polar	33892256
Mammeisin,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C(O[Si](C)(C)C)C2=C1OC(=O)C=C2C1=CC=CC=C1	3227.9	Semi standard non polar	33892256
Mammeisin,1TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C(O)C2=C1OC(=O)C=C2C1=CC=CC=C1	3409.7	Semi standard non polar	33892256
Mammeisin,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C(C(=O)CC(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(=O)C=C2C1=CC=CC=C1	3413.8	Semi standard non polar	33892256
Mammeisin,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(=O)C=C2C1=CC=CC=C1	3580.9	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 - Mammeisin GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-2209000000-68a001744e75bdc38013	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mammeisin GC-MS (2 TMS) - 70eV, Positive	splash10-0f7c-6602980000-461b9806feaa38448426	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mammeisin 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 - Mammeisin 10V, Positive-QTOF	splash10-0a4i-1009600000-4972bd740409c37e20aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mammeisin 20V, Positive-QTOF	splash10-000t-3019100000-67fde51f9e10b6c85108	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mammeisin 40V, Positive-QTOF	splash10-05o3-9088000000-fa6638578d3d634d1923	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mammeisin 10V, Negative-QTOF	splash10-0a4i-0005900000-79055f06e327a76f44f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mammeisin 20V, Negative-QTOF	splash10-05fr-4029300000-bf48b8e2e80dfacaf1de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mammeisin 40V, Negative-QTOF	splash10-0553-9334000000-04185b2be25d97933cca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mammeisin 10V, Negative-QTOF	splash10-0a4i-0000900000-7b5974fd53d3ffdb29ad	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mammeisin 20V, Negative-QTOF	splash10-0a4i-0019800000-ee8ce9399b2b96a8ed10	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mammeisin 40V, Negative-QTOF	splash10-00b9-5269000000-136f79e5e057926e05cc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mammeisin 10V, Positive-QTOF	splash10-0a4i-0001900000-1fb85e80b292b84235ee	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mammeisin 20V, Positive-QTOF	splash10-0a4i-1047900000-e036e81eb8dae8526785	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mammeisin 40V, Positive-QTOF	splash10-052e-1097000000-2b467c856e230a3f7829	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281419

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1841591

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 Mammeisin (HMDB0034269)

MOL for HMDB0034269 (Mammeisin)

3D MOL for HMDB0034269 (Mammeisin)

3D SDF for HMDB0034269 (Mammeisin)

3D-SDF for HMDB0034269 (Mammeisin)

PDB for HMDB0034269 (Mammeisin)

3D PDB for HMDB0034269 (Mammeisin)

SMILES for HMDB0034269 (Mammeisin)

INCHI for HMDB0034269 (Mammeisin)

Structure for HMDB0034269 (Mammeisin)

3D Structure for HMDB0034269 (Mammeisin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra