Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:46:49 UTC

Update Date

2022-03-07 02:53:11 UTC

HMDB ID

HMDB0031958

Secondary Accession Numbers

HMDB31958

Metabolite Identification

Common Name

3-O-Acetylepisamarcandin

Description

3-O-Acetylepisamarcandin 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). 3-O-Acetylepisamarcandin has been detected, but not quantified in, green vegetables and herbs and spices. This could make 3-O-acetylepisamarcandin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-O-Acetylepisamarcandin.

Structure

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


  Mrv0541 05061306152D          

 32 35  0  0  0  0            999 V2000
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0421   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    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
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    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
    2.1434    3.7125    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
    5.0013   -1.2375    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
    2.8579    3.3000    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
    2.8579    0.0000    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165    0.6817    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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  2  0  0  0  0
  9  7  2  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 16  1  1  0  0  0  0
 17  6  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 18 14  2  0  0  0  0
 19 14  1  0  0  0  0
 19 17  2  0  0  0  0
 20 10  1  0  0  0  0
 21 15  1  0  0  0  0
 22 11  1  0  0  0  0
 23  9  1  0  0  0  0
 24  2  1  0  0  0  0
 24  3  1  0  0  0  0
 24 20  1  0  0  0  0
 24 22  1  0  0  0  0
 25  4  1  0  0  0  0
 25 12  1  0  0  0  0
 25 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26  5  1  0  0  0  0
 26 13  1  0  0  0  0
 26 21  1  0  0  0  0
 27 16  2  0  0  0  0
 28 23  2  0  0  0  0
 29 26  1  0  0  0  0
 30 15  1  0  0  0  0
 30 18  1  0  0  0  0
 31 16  1  0  0  0  0
 31 22  1  0  0  0  0
 32 19  1  0  0  0  0
 32 23  1  0  0  0  0
M  END

HMDB0031958
     RDKit          3D
3-O-Acetylepisamarcandin
 66 69  0  0  0  0  0  0  0  0999 V2000
   -4.2214    4.4385   -0.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4793    2.9750   -0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6367    2.5302   -0.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4121    2.1138   -0.5522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413    0.6873   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9526    0.1901   -1.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715   -0.0783   -1.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566   -0.9817   -0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6981   -2.3462   -0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3631   -1.0471   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1352   -1.1010   -1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4951   -1.1662   -1.6229 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5056   -0.4222   -1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8052   -0.9393   -1.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9073   -0.2427   -0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7587    0.9787   -0.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8497    1.6844    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6493    2.8941    0.7279 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3745    3.3808    0.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2469    4.4976    1.4503 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    2.6825    0.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5054    1.5167   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4118    0.7854   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414   -2.0752    0.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652   -3.4514    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296   -1.6620    1.0622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1280   -2.1033    1.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5079   -1.6072    1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7048   -0.4992    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0689    0.0492    0.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174   -0.9151    1.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1197    1.1920    1.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2726    4.6786   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2200    4.8191   -1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0497    4.9240   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6557    0.5032   -0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0895    0.9921   -2.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5270   -0.6793   -2.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2860   -0.6939   -2.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988    0.8470   -1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3062   -2.6526   -1.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892   -2.2150   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5723   -3.1052   -0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5889   -0.0634    0.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -1.9493   -2.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8892   -0.2013   -2.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9682   -1.8898   -1.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9204   -0.6128   -1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8382    1.2716   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5235    3.4548    1.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4536    1.2386   -0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -3.5956   -0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0122   -3.8170    0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732   -4.1754    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3599   -2.2658    1.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1877   -3.1843    2.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3514   -1.6048    2.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2904   -2.3877    1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8402   -1.1248    2.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0002    0.3166    1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0000   -0.9692    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1015   -0.4022    1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -1.8711    0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1138    1.6869    1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8437    0.8192    2.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3939    1.9506    1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 10 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30  5  1  0
 29  8  1  0
 23 13  1  0
 22 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 14 47  1  0
 15 48  1  0
 17 49  1  0
 18 50  1  0
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 29 60  1  0
 31 61  1  0
 31 62  1  0
 31 63  1  0
 32 64  1  0
 32 65  1  0
 32 66  1  0
M  END


  Mrv0541 05061306152D          

 32 35  0  0  0  0            999 V2000
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0421   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    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
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    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
    2.1434    3.7125    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
    5.0013   -1.2375    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
    2.8579    3.3000    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
    2.8579    0.0000    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165    0.6817    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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  2  0  0  0  0
  9  7  2  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 16  1  1  0  0  0  0
 17  6  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 18 14  2  0  0  0  0
 19 14  1  0  0  0  0
 19 17  2  0  0  0  0
 20 10  1  0  0  0  0
 21 15  1  0  0  0  0
 22 11  1  0  0  0  0
 23  9  1  0  0  0  0
 24  2  1  0  0  0  0
 24  3  1  0  0  0  0
 24 20  1  0  0  0  0
 24 22  1  0  0  0  0
 25  4  1  0  0  0  0
 25 12  1  0  0  0  0
 25 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26  5  1  0  0  0  0
 26 13  1  0  0  0  0
 26 21  1  0  0  0  0
 27 16  2  0  0  0  0
 28 23  2  0  0  0  0
 29 26  1  0  0  0  0
 30 15  1  0  0  0  0
 30 18  1  0  0  0  0
 31 16  1  0  0  0  0
 31 22  1  0  0  0  0
 32 19  1  0  0  0  0
 32 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031958

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1CCC2(C)C(COC3=CC4=C(C=CC(=O)O4)C=C3)C(C)(O)CCC2C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O6/c1-16(27)31-22-11-12-25(4)20(24(22,2)3)10-13-26(5,29)21(25)15-30-18-8-6-17-7-9-23(28)32-19(17)14-18/h6-9,14,20-22,29H,10-13,15H2,1-5H3

> <INCHI_KEY>
RIPKCRCUFJSKKD-UHFFFAOYSA-N

> <FORMULA>
C26H34O6

> <MOLECULAR_WEIGHT>
442.5446

> <EXACT_MASS>
442.23553882

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
48.580444893820484

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-1,1,4a,6-tetramethyl-5-{[(2-oxo-2H-chromen-7-yl)oxy]methyl}-decahydronaphthalen-2-yl acetate

> <ALOGPS_LOGP>
4.84

> <JCHEM_LOGP>
3.7722637859999977

> <ALOGPS_LOGS>
-5.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.699053584718499

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9304339620441286

> <JCHEM_POLAR_SURFACE_AREA>
82.06000000000002

> <JCHEM_REFRACTIVITY>
120.62849999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-1,1,4a,6-tetramethyl-5-{[(2-oxochromen-7-yl)oxy]methyl}-hexahydro-2H-naphthalen-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031958
     RDKit          3D
3-O-Acetylepisamarcandin
 66 69  0  0  0  0  0  0  0  0999 V2000
   -4.2214    4.4385   -0.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4793    2.9750   -0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6367    2.5302   -0.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4121    2.1138   -0.5522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413    0.6873   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9526    0.1901   -1.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715   -0.0783   -1.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566   -0.9817   -0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6981   -2.3462   -0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3631   -1.0471   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1352   -1.1010   -1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4951   -1.1662   -1.6229 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5056   -0.4222   -1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8052   -0.9393   -1.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9073   -0.2427   -0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7587    0.9787   -0.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8497    1.6844    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6493    2.8941    0.7279 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3745    3.3808    0.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2469    4.4976    1.4503 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    2.6825    0.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5054    1.5167   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4118    0.7854   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414   -2.0752    0.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652   -3.4514    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296   -1.6620    1.0622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1280   -2.1033    1.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5079   -1.6072    1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7048   -0.4992    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0689    0.0492    0.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174   -0.9151    1.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1197    1.1920    1.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2726    4.6786   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2200    4.8191   -1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0497    4.9240   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6557    0.5032   -0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0895    0.9921   -2.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5270   -0.6793   -2.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2860   -0.6939   -2.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988    0.8470   -1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3062   -2.6526   -1.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892   -2.2150   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5723   -3.1052   -0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5889   -0.0634    0.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -1.9493   -2.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8892   -0.2013   -2.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9682   -1.8898   -1.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9204   -0.6128   -1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8382    1.2716   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5235    3.4548    1.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4536    1.2386   -0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -3.5956   -0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0122   -3.8170    0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732   -4.1754    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3599   -2.2658    1.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1877   -3.1843    2.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3514   -1.6048    2.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2904   -2.3877    1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8402   -1.1248    2.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0002    0.3166    1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0000   -0.9692    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1015   -0.4022    1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -1.8711    0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1138    1.6869    1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8437    0.8192    2.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3939    1.9506    1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 10 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30  5  1  0
 29  8  1  0
 23 13  1  0
 22 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 14 47  1  0
 15 48  1  0
 17 49  1  0
 18 50  1  0
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 29 60  1  0
 31 61  1  0
 31 62  1  0
 31 63  1  0
 32 64  1  0
 32 65  1  0
 32 66  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      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.679  -1.950   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.658  -1.950   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.141   2.987   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.334  11.550   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.151   1.273   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   24                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5   26                                                            
CONECT    6    8   17                                                       
CONECT    7    9   17                                                       
CONECT    8    6   18                                                       
CONECT    9    7   23                                                       
CONECT   10   13   20                                                       
CONECT   11   12   22                                                       
CONECT   12   11   25                                                       
CONECT   13   10   26                                                       
CONECT   14   18   19                                                       
CONECT   15   21   30                                                       
CONECT   16    1   27   31                                                  
CONECT   17    6    7   19                                                  
CONECT   18    8   14   30                                                  
CONECT   19   14   17   32                                                  
CONECT   20   10   24   25                                                  
CONECT   21   15   25   26                                                  
CONECT   22   11   24   31                                                  
CONECT   23    9   28   32                                                  
CONECT   24    2    3   20   22                                             
CONECT   25    4   12   20   21                                             
CONECT   26    5   13   21   29                                             
CONECT   27   16                                                            
CONECT   28   23                                                            
CONECT   29   26                                                            
CONECT   30   15   18                                                       
CONECT   31   16   22                                                       
CONECT   32   19   23                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0031958
HETATM    1  C1  UNL     1      -4.221   4.438  -0.579  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.479   2.975  -0.599  1.00  0.00           C  
HETATM    3  O1  UNL     1      -5.637   2.530  -0.656  1.00  0.00           O  
HETATM    4  O2  UNL     1      -3.412   2.114  -0.552  1.00  0.00           O  
HETATM    5  C3  UNL     1      -3.541   0.687  -0.566  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.953   0.190  -1.825  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.472  -0.078  -1.785  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.157  -0.982  -0.617  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.698  -2.346  -0.997  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.363  -1.047  -0.405  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.135  -1.101  -1.671  1.00  0.00           C  
HETATM   12  O3  UNL     1       2.495  -1.166  -1.623  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.506  -0.422  -1.174  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.805  -0.939  -1.350  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.907  -0.243  -0.921  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.759   0.979  -0.309  1.00  0.00           C  
HETATM   17  C14 UNL     1       6.850   1.684   0.125  1.00  0.00           C  
HETATM   18  C15 UNL     1       6.649   2.894   0.728  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.375   3.381   0.890  1.00  0.00           C  
HETATM   20  O4  UNL     1       5.247   4.498   1.450  1.00  0.00           O  
HETATM   21  O5  UNL     1       4.341   2.683   0.464  1.00  0.00           O  
HETATM   22  C17 UNL     1       4.505   1.517  -0.119  1.00  0.00           C  
HETATM   23  C18 UNL     1       3.412   0.785  -0.566  1.00  0.00           C  
HETATM   24  C19 UNL     1       0.741  -2.075   0.608  1.00  0.00           C  
HETATM   25  C20 UNL     1       0.965  -3.451   0.047  1.00  0.00           C  
HETATM   26  O6  UNL     1       2.030  -1.662   1.062  1.00  0.00           O  
HETATM   27  C21 UNL     1      -0.128  -2.103   1.813  1.00  0.00           C  
HETATM   28  C22 UNL     1      -1.508  -1.607   1.705  1.00  0.00           C  
HETATM   29  C23 UNL     1      -1.705  -0.499   0.679  1.00  0.00           C  
HETATM   30  C24 UNL     1      -3.069   0.049   0.695  1.00  0.00           C  
HETATM   31  C25 UNL     1      -4.117  -0.915   1.272  1.00  0.00           C  
HETATM   32  C26 UNL     1      -3.120   1.192   1.737  1.00  0.00           C  
HETATM   33  H1  UNL     1      -3.273   4.679  -0.072  1.00  0.00           H  
HETATM   34  H2  UNL     1      -4.220   4.819  -1.624  1.00  0.00           H  
HETATM   35  H3  UNL     1      -5.050   4.924  -0.018  1.00  0.00           H  
HETATM   36  H4  UNL     1      -4.656   0.503  -0.620  1.00  0.00           H  
HETATM   37  H5  UNL     1      -3.089   0.992  -2.612  1.00  0.00           H  
HETATM   38  H6  UNL     1      -3.527  -0.679  -2.264  1.00  0.00           H  
HETATM   39  H7  UNL     1      -1.286  -0.694  -2.716  1.00  0.00           H  
HETATM   40  H8  UNL     1      -0.899   0.847  -1.785  1.00  0.00           H  
HETATM   41  H9  UNL     1      -1.306  -2.653  -1.993  1.00  0.00           H  
HETATM   42  H10 UNL     1      -2.789  -2.215  -1.154  1.00  0.00           H  
HETATM   43  H11 UNL     1      -1.572  -3.105  -0.226  1.00  0.00           H  
HETATM   44  H12 UNL     1       0.589  -0.063   0.056  1.00  0.00           H  
HETATM   45  H13 UNL     1       0.799  -1.949  -2.347  1.00  0.00           H  
HETATM   46  H14 UNL     1       0.889  -0.201  -2.324  1.00  0.00           H  
HETATM   47  H15 UNL     1       4.968  -1.890  -1.824  1.00  0.00           H  
HETATM   48  H16 UNL     1       6.920  -0.613  -1.041  1.00  0.00           H  
HETATM   49  H17 UNL     1       7.838   1.272  -0.019  1.00  0.00           H  
HETATM   50  H18 UNL     1       7.524   3.455   1.073  1.00  0.00           H  
HETATM   51  H19 UNL     1       2.454   1.239  -0.409  1.00  0.00           H  
HETATM   52  H20 UNL     1       0.651  -3.596  -0.983  1.00  0.00           H  
HETATM   53  H21 UNL     1       2.012  -3.817   0.121  1.00  0.00           H  
HETATM   54  H22 UNL     1       0.373  -4.175   0.676  1.00  0.00           H  
HETATM   55  H23 UNL     1       2.360  -2.266   1.762  1.00  0.00           H  
HETATM   56  H24 UNL     1      -0.188  -3.184   2.151  1.00  0.00           H  
HETATM   57  H25 UNL     1       0.351  -1.605   2.711  1.00  0.00           H  
HETATM   58  H26 UNL     1      -2.290  -2.388   1.535  1.00  0.00           H  
HETATM   59  H27 UNL     1      -1.840  -1.125   2.675  1.00  0.00           H  
HETATM   60  H28 UNL     1      -1.000   0.317   1.034  1.00  0.00           H  
HETATM   61  H29 UNL     1      -4.000  -0.969   2.372  1.00  0.00           H  
HETATM   62  H30 UNL     1      -5.102  -0.402   1.105  1.00  0.00           H  
HETATM   63  H31 UNL     1      -4.159  -1.871   0.773  1.00  0.00           H  
HETATM   64  H32 UNL     1      -4.114   1.687   1.711  1.00  0.00           H  
HETATM   65  H33 UNL     1      -2.844   0.819   2.736  1.00  0.00           H  
HETATM   66  H34 UNL     1      -2.394   1.951   1.340  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   30   36
CONECT    6    7   37   38
CONECT    7    8   39   40
CONECT    8    9   10   29
CONECT    9   41   42   43
CONECT   10   11   24   44
CONECT   11   12   45   46
CONECT   12   13
CONECT   13   14   14   23
CONECT   14   15   47
CONECT   15   16   16   48
CONECT   16   17   22
CONECT   17   18   18   49
CONECT   18   19   50
CONECT   19   20   20   21
CONECT   21   22
CONECT   22   23   23
CONECT   23   51
CONECT   24   25   26   27
CONECT   25   52   53   54
CONECT   26   55
CONECT   27   28   56   57
CONECT   28   29   58   59
CONECT   29   30   60
CONECT   30   31   32
CONECT   31   61   62   63
CONECT   32   64   65   66
END

HMDB0031958
     RDKit          3D
3-O-Acetylepisamarcandin
 66 69  0  0  0  0  0  0  0  0999 V2000
   -4.2214    4.4385   -0.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4793    2.9750   -0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6367    2.5302   -0.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4121    2.1138   -0.5522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413    0.6873   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9526    0.1901   -1.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4715   -0.0783   -1.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566   -0.9817   -0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6981   -2.3462   -0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3631   -1.0471   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1352   -1.1010   -1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4951   -1.1662   -1.6229 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5056   -0.4222   -1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8052   -0.9393   -1.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9073   -0.2427   -0.9210 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7587    0.9787   -0.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8497    1.6844    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6493    2.8941    0.7279 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3745    3.3808    0.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2469    4.4976    1.4503 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    2.6825    0.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5054    1.5167   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4118    0.7854   -0.5657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414   -2.0752    0.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652   -3.4514    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0296   -1.6620    1.0622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1280   -2.1033    1.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5079   -1.6072    1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7048   -0.4992    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0689    0.0492    0.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174   -0.9151    1.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1197    1.1920    1.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2726    4.6786   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2200    4.8191   -1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0497    4.9240   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6557    0.5032   -0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0895    0.9921   -2.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5270   -0.6793   -2.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2860   -0.6939   -2.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988    0.8470   -1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3062   -2.6526   -1.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892   -2.2150   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5723   -3.1052   -0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5889   -0.0634    0.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -1.9493   -2.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8892   -0.2013   -2.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9682   -1.8898   -1.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9204   -0.6128   -1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8382    1.2716   -0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5235    3.4548    1.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4536    1.2386   -0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -3.5956   -0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0122   -3.8170    0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3732   -4.1754    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3599   -2.2658    1.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1877   -3.1843    2.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3514   -1.6048    2.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2904   -2.3877    1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8402   -1.1248    2.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0002    0.3166    1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0000   -0.9692    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1015   -0.4022    1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -1.8711    0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1138    1.6869    1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8437    0.8192    2.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3939    1.9506    1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 10 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30  5  1  0
 29  8  1  0
 23 13  1  0
 22 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 14 47  1  0
 15 48  1  0
 17 49  1  0
 18 50  1  0
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 29 60  1  0
 31 61  1  0
 31 62  1  0
 31 63  1  0
 32 64  1  0
 32 65  1  0
 32 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Hydroxy-1,1,4a,6-tetramethyl-5-{[(2-oxo-2H-chromen-7-yl)oxy]methyl}-decahydronaphthalen-2-yl acetic acid	HMDB

Chemical Formula

C₂₆H₃₄O₆

Average Molecular Weight

442.5446

Monoisotopic Molecular Weight

442.23553882

IUPAC Name

6-hydroxy-1,1,4a,6-tetramethyl-5-{[(2-oxo-2H-chromen-7-yl)oxy]methyl}-decahydronaphthalen-2-yl acetate

Traditional Name

6-hydroxy-1,1,4a,6-tetramethyl-5-{[(2-oxochromen-7-yl)oxy]methyl}-hexahydro-2H-naphthalen-2-yl acetate

CAS Registry Number

61490-18-4

SMILES

CC(=O)OC1CCC2(C)C(COC3=CC4=C(C=CC(=O)O4)C=C3)C(C)(O)CCC2C1(C)C

InChI Identifier

InChI=1S/C26H34O6/c1-16(27)31-22-11-12-25(4)20(24(22,2)3)10-13-26(5,29)21(25)15-30-18-8-6-17-7-9-23(28)32-19(17)14-18/h6-9,14,20-22,29H,10-13,15H2,1-5H3

InChI Key

RIPKCRCUFJSKKD-UHFFFAOYSA-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
Benzenoid
Pyran
Heteroaromatic compound
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031958)

Source

Endogenous

Endogenous (HMDB: HMDB0031958)

Plant

Plant (HMDB: HMDB0031958)

Exogenous

Food

Food (HMDB: HMDB0031958)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0031958)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0031958)

Role

Biological role

Energy source (HMDB: HMDB0031958)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031958)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0015 g/L	ALOGPS
logP	4.84	ALOGPS
logP	3.77	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	14.7	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.63 m³·mol⁻¹	ChemAxon
Polarizability	48.58 Å³	ChemAxon
Number of Rings	4	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]+	203.728	31661259
DarkChem	[M-H]-	196.369	31661259
DeepCCS	[M+H]+	207.167	30932474
DeepCCS	[M-H]-	204.804	30932474
DeepCCS	[M-2H]-	237.793	30932474
DeepCCS	[M+Na]+	213.255	30932474
AllCCS	[M+H]+	208.3	32859911
AllCCS	[M+H-H2O]+	206.3	32859911
AllCCS	[M+NH4]+	210.2	32859911
AllCCS	[M+Na]+	210.8	32859911
AllCCS	[M-H]-	206.1	32859911
AllCCS	[M+Na-2H]-	207.1	32859911
AllCCS	[M+HCOO]-	208.3	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.	8.57 minutes	32390414
Predicted by Siyang on May 30, 2022	18.3723 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.07 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2947.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	359.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	246.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	195.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	883.7 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	830.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1430.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	598.3 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	1924.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	531.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	493.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	283.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	423.8 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	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-O-Acetylepisamarcandin	CC(=O)OC1CCC2(C)C(COC3=CC4=C(C=CC(=O)O4)C=C3)C(C)(O)CCC2C1(C)C	4241.1	Standard polar	33892256
3-O-Acetylepisamarcandin	CC(=O)OC1CCC2(C)C(COC3=CC4=C(C=CC(=O)O4)C=C3)C(C)(O)CCC2C1(C)C	3498.7	Standard non polar	33892256
3-O-Acetylepisamarcandin	CC(=O)OC1CCC2(C)C(COC3=CC4=C(C=CC(=O)O4)C=C3)C(C)(O)CCC2C1(C)C	3791.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-O-Acetylepisamarcandin,1TMS,isomer #1	CC(=O)OC1CCC2(C)C(COC3=CC=C4C=CC(=O)OC4=C3)C(C)(O[Si](C)(C)C)CCC2C1(C)C	3632.3	Semi standard non polar	33892256
3-O-Acetylepisamarcandin,1TBDMS,isomer #1	CC(=O)OC1CCC2(C)C(COC3=CC=C4C=CC(=O)OC4=C3)C(C)(O[Si](C)(C)C(C)(C)C)CCC2C1(C)C	3848.5	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 - 3-O-Acetylepisamarcandin GC-MS (Non-derivatized) - 70eV, Positive	splash10-01td-2529500000-9f29f93f387a21e515ef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-O-Acetylepisamarcandin GC-MS (1 TMS) - 70eV, Positive	splash10-0002-4205910000-ddb5e3cb9071a6882165	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-O-Acetylepisamarcandin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin , positive-QTOF	splash10-03di-0921000000-7710a65ac8d55bdab29d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin , positive-QTOF	splash10-03di-0920000000-b8275cb923c7e4d494e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin , positive-QTOF	splash10-03di-0910000000-fedb411ffcf5f30fe085	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin , positive-QTOF	splash10-03di-0910000000-c1f5af217bd253aef979	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin , positive-QTOF	splash10-03e9-0914000000-72b5e0265dab7ea20564	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin 10V, Positive-QTOF	splash10-005c-0032900000-3dbc5b9b265fd25f340d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin 20V, Positive-QTOF	splash10-001i-0039400000-575eb2e71e268e1aef96	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin 40V, Positive-QTOF	splash10-03yr-1594000000-9550514597b339124b4c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin 10V, Negative-QTOF	splash10-0006-1406900000-35da8eb25311bbbeb67d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin 20V, Negative-QTOF	splash10-08gm-3509500000-ab4dc691943ea8920e45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin 40V, Negative-QTOF	splash10-02t9-2901000000-3e46fb51cde9c064f1c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin 10V, Positive-QTOF	splash10-029x-0349700000-034b4d050503a1fc4654	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin 20V, Positive-QTOF	splash10-03di-0596300000-110b770c49679b174d71	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin 40V, Positive-QTOF	splash10-014i-2940000000-543a379b023fa5b6e2a3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin 10V, Negative-QTOF	splash10-06r6-8500900000-8f2f431f803cab7a4ce0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin 20V, Negative-QTOF	splash10-03di-2900000000-fe1f8c2acbeadf76aa88	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Acetylepisamarcandin 40V, Negative-QTOF	splash10-0159-0900000000-83b34e966b1a89c1e075	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

FDB008650

KNApSAcK ID

C00054739

Chemspider ID

2350861

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3095106

PDB ID

Not Available

ChEBI ID

175560

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Enzymes

Enzyme Details

1. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Reactions

3-O-Acetylepisamarcandin → Nevskin	details

Showing metabocard for 3-O-Acetylepisamarcandin (HMDB0031958)

MOL for HMDB0031958 (3-O-Acetylepisamarcandin)

3D MOL for HMDB0031958 (3-O-Acetylepisamarcandin)

3D SDF for HMDB0031958 (3-O-Acetylepisamarcandin)

3D-SDF for HMDB0031958 (3-O-Acetylepisamarcandin)

PDB for HMDB0031958 (3-O-Acetylepisamarcandin)

3D PDB for HMDB0031958 (3-O-Acetylepisamarcandin)

SMILES for HMDB0031958 (3-O-Acetylepisamarcandin)

INCHI for HMDB0031958 (3-O-Acetylepisamarcandin)

Structure for HMDB0031958 (3-O-Acetylepisamarcandin)

3D Structure for HMDB0031958 (3-O-Acetylepisamarcandin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions