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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:03:06 UTC

Update Date

2022-03-07 02:56:37 UTC

HMDB ID

HMDB0040498

Secondary Accession Numbers

HMDB40498

Metabolite Identification

Common Name

3-Epipapyriferic acid

Description

3-Epipapyriferic acid, also known as 3-epipapyriferate, belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. 3-Epipapyriferic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv0541 05061311532D          

 43 47  0  0  0  0            999 V2000
    2.7885    2.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984   -1.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5378   -1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5388    4.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9555    3.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7863    1.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6252   -0.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3269   -0.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1644    2.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992    1.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4979   -1.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562    0.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2772    2.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712    0.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7134    0.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2129   -0.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7244    2.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5012    1.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0728    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5035    3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7151    1.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162    1.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7840   -0.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5001    0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551   -0.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8657    3.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7867    0.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739   -0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9302    1.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0690   -1.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2023    4.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851    0.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2140    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9291    0.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9712    2.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5046    3.9132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7855    1.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5017    0.2074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7889   -1.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4490    4.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2174    2.6747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401   -1.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0585    3.2948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 13  1  0  0  0  0
 20  1  1  0  0  0  0
 21 10  1  0  0  0  0
 22 18  1  0  0  0  0
 23 11  1  0  0  0  0
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 26 13  1  0  0  0  0
 27 19  1  0  0  0  0
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 29 21  1  0  0  0  0
 29 22  1  0  0  0  0
 30  2  1  0  0  0  0
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 30 23  1  0  0  0  0
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 31  4  1  0  0  0  0
 31  5  1  0  0  0  0
 31 26  1  0  0  0  0
 32  6  1  0  0  0  0
 32 14  1  0  0  0  0
 32 23  1  0  0  0  0
 32 24  1  0  0  0  0
 33  7  1  0  0  0  0
 33 16  1  0  0  0  0
 33 24  1  0  0  0  0
 34  8  1  0  0  0  0
 34 15  1  0  0  0  0
 34 29  1  0  0  0  0
 34 33  1  0  0  0  0
 35  9  1  0  0  0  0
 35 17  1  0  0  0  0
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 36 20  2  0  0  0  0
 37 27  2  0  0  0  0
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 39 28  2  0  0  0  0
 40 31  1  0  0  0  0
 41 20  1  0  0  0  0
 41 22  1  0  0  0  0
 42 25  1  0  0  0  0
 42 28  1  0  0  0  0
 43 26  1  0  0  0  0
 43 35  1  0  0  0  0
M  END

HMDB0040498
     RDKit          3D
3-Epipapyriferic acid
 99103  0  0  0  0  0  0  0  0999 V2000
    3.2835   -0.8435   -3.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545    0.2029   -2.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2854    1.3621   -2.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9543   -0.2100   -1.8414 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0722    0.2230   -1.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061311532D          

 43 47  0  0  0  0            999 V2000
    2.7885    2.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984   -1.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5378   -1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6252   -0.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3269   -0.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1644    2.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992    1.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4979   -1.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562    0.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2772    2.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712    0.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2129   -0.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7244    2.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5012    1.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0728    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5035    3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7151    1.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162    1.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5001    0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551   -0.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8657    3.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7867    0.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9302    1.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0690   -1.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2023    4.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851    0.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2140    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9291    0.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9712    2.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5046    3.9132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7855    1.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5017    0.2074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7889   -1.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4490    4.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2174    2.6747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401   -1.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0585    3.2948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 33  7  1  0  0  0  0
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 43 35  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040498

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1CC2C3(C)CCC(OC(=O)CC(O)=O)C(C)(C)C3CCC2(C)C2(C)CCC(C12)C1(C)CCC(O1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C35H56O8/c1-20(36)41-22-18-24-32(6)14-12-25(42-28(39)19-27(37)38)30(2,3)23(32)11-16-33(24,7)34(8)15-10-21(29(22)34)35(9)17-13-26(43-35)31(4,5)40/h21-26,29,40H,10-19H2,1-9H3,(H,37,38)

> <INCHI_KEY>
RLVAVWQAAQFUOP-UHFFFAOYSA-N

> <FORMULA>
C35H56O8

> <MOLECULAR_WEIGHT>
604.8143

> <EXACT_MASS>
604.397518768

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
68.42501354678676

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[16-(acetyloxy)-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-oxopropanoic acid

> <ALOGPS_LOGP>
5.82

> <JCHEM_LOGP>
5.327681833333331

> <ALOGPS_LOGS>
-6.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.325328775704747

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.29453936317829

> <JCHEM_PKA_STRONGEST_BASIC>
-3.09390119352444

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
160.7205

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[16-(acetyloxy)-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040498
     RDKit          3D
3-Epipapyriferic acid
 99103  0  0  0  0  0  0  0  0999 V2000
    3.2835   -0.8435   -3.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545    0.2029   -2.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2854    1.3621   -2.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9543   -0.2100   -1.8414 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    0.5938   -0.8240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0321    0.8064   -1.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9872    0.5357   -0.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4177    0.9296   -0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689    2.3833   -0.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722    0.2230   -1.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5888    0.3525   -1.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1332    0.0408   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5348   -0.0907   -0.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1273   -1.2937    0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3639   -2.2574    0.3898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5777   -1.5689    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3763   -0.3680   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6223   -0.4089   -0.1904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7321    0.8284   -0.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6324    1.0276    0.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1795    2.4180    0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2351    0.5553    2.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1262    0.9700    0.9106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7278    0.0056    1.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2853   -0.3861    2.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883   -0.7137    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5668   -1.9386    0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6522   -1.1374    0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9020   -2.0857   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734   -1.8052    1.8379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6817   -1.6410    1.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7561   -0.1382    1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0848    0.2954    0.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1055    1.7931    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0344    0.0561    2.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3703    0.1693    1.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0341   -0.4787    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8903    0.0944   -1.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3488   -0.1057   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7540   -0.6252   -2.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7182    1.4320   -1.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6869   -0.4008   -0.1696 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335    0.1168    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7911   -1.6727   -3.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574   -1.2400   -4.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9699   -0.3954   -4.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9325    1.5857   -0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1690    1.8956   -1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3100    0.2967   -2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7483    1.4114    0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763    2.9248   -0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0456    2.3583   -2.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1730    2.9651   -0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8041    0.6782   -2.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7564   -0.8270   -1.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9517   -0.4827   -2.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9560    1.2728   -1.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7215   -0.9498    0.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8349   -2.4049   -0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9121   -1.9460    1.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2431    1.7087   -0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4863    3.1203    1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4685    2.6758   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8390    1.0946    3.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2946   -0.5352    2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3232    0.8790    2.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8644    1.9912    1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9212    0.4683    2.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3320   -0.9239    2.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354    0.4363    2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6312   -1.9256    0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039   -2.7033    1.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5284   -3.0972   -0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937   -1.8571   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466   -2.2614   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933   -2.8697    1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404   -1.2428    2.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1517   -1.8875    2.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962   -2.2857    0.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875    0.2937    2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141    2.1363   -0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8730    2.3105    1.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1322    2.2186    1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8891    0.7971    2.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9540   -0.9483    2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1117   -0.4064    1.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    1.2132    1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3109   -1.5643    0.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7084    0.7723   -0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4641   -1.0307   -0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9846   -0.1595   -1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7100   -0.4532   -2.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5617   -1.6942   -2.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9771   -0.0935   -2.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4143    1.9645   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9567    0.8710    1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
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  6 49  1  0
  7 50  1  0
  9 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 12 58  1  0
 16 59  1  0
 16 60  1  0
 19 61  1  0
 21 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 22 66  1  0
 22 67  1  0
 23 68  1  0
 24 69  1  0
 24 70  1  0
 25 71  1  0
 25 72  1  0
 27 73  1  0
 27 74  1  0
 27 75  1  0
 29 76  1  0
 29 77  1  0
 29 78  1  0
 30 79  1  0
 30 80  1  0
 31 81  1  0
 31 82  1  0
 32 83  1  0
 34 84  1  0
 34 85  1  0
 34 86  1  0
 35 87  1  0
 35 88  1  0
 36 89  1  0
 36 90  1  0
 37 91  1  0
 39 92  1  0
 39 93  1  0
 39 94  1  0
 40 95  1  0
 40 96  1  0
 40 97  1  0
 41 98  1  0
 43 99  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       5.205   4.997   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.850  -3.113   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.871  -3.110   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.072   9.281   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.850   7.246   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.201   1.916   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.634  -0.778   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.944  -0.107   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.640   4.941   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.572   1.908   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.529  -1.935   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.532   0.380   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.584   5.134   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.866   1.148   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.665   0.663   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.864  -1.167   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.552   3.991   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.536   2.685   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.136   0.384   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.540   5.765   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.668   3.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.870   3.453   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.197  -1.163   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.534   1.144   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.530  -1.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.816   6.468   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.469   1.155   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.138  -1.156   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.203   2.681   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.862  -1.932   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.444   7.874   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.199   0.376   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.866   0.373   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.201   1.141   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.146   4.619   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.542   7.305   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -1.466   2.695   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -2.803   0.387   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -1.473  -1.925   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      12.038   8.503   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       7.872   4.993   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       1.195  -1.928   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      11.309   6.150   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   30                                                            
CONECT    3   30                                                            
CONECT    4   31                                                            
CONECT    5   31                                                            
CONECT    6   32                                                            
CONECT    7   33                                                            
CONECT    8   34                                                            
CONECT    9   35                                                            
CONECT   10   15   21                                                       
CONECT   11   16   23                                                       
CONECT   12   14   25                                                       
CONECT   13   17   26                                                       
CONECT   14   12   32                                                       
CONECT   15   10   34                                                       
CONECT   16   11   33                                                       
CONECT   17   13   35                                                       
CONECT   18   22   24                                                       
CONECT   19   27   28                                                       
CONECT   20    1   36   41                                                  
CONECT   21   10   29   35                                                  
CONECT   22   18   29   41                                                  
CONECT   23   11   30   32                                                  
CONECT   24   18   32   33                                                  
CONECT   25   12   30   42                                                  
CONECT   26   13   31   43                                                  
CONECT   27   19   37   38                                                  
CONECT   28   19   39   42                                                  
CONECT   29   21   22   34                                                  
CONECT   30    2    3   23   25                                             
CONECT   31    4    5   26   40                                             
CONECT   32    6   14   23   24                                             
CONECT   33    7   16   24   34                                             
CONECT   34    8   15   29   33                                             
CONECT   35    9   17   21   43                                             
CONECT   36   20                                                            
CONECT   37   27                                                            
CONECT   38   27                                                            
CONECT   39   28                                                            
CONECT   40   31                                                            
CONECT   41   20   22                                                       
CONECT   42   25   28                                                       
CONECT   43   26   35                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

COMPND    HMDB0040498
HETATM    1  C1  UNL     1       3.283  -0.843  -3.775  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.854   0.203  -2.775  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.285   1.362  -2.794  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.954  -0.210  -1.841  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.429   0.594  -0.824  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.032   0.806  -1.210  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.987   0.536  -0.099  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.418   0.930  -0.394  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.269   2.383  -0.925  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.072   0.223  -1.514  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.589   0.353  -1.511  1.00  0.00           C  
HETATM   12  C10 UNL     1      -5.133   0.041  -0.144  1.00  0.00           C  
HETATM   13  O3  UNL     1      -6.535  -0.091  -0.143  1.00  0.00           O  
HETATM   14  C11 UNL     1      -7.127  -1.294   0.138  1.00  0.00           C  
HETATM   15  O4  UNL     1      -6.364  -2.257   0.390  1.00  0.00           O  
HETATM   16  C12 UNL     1      -8.578  -1.569   0.173  1.00  0.00           C  
HETATM   17  C13 UNL     1      -9.376  -0.368  -0.136  1.00  0.00           C  
HETATM   18  O5  UNL     1     -10.622  -0.409  -0.190  1.00  0.00           O  
HETATM   19  O6  UNL     1      -8.732   0.828  -0.369  1.00  0.00           O  
HETATM   20  C14 UNL     1      -4.632   1.028   0.846  1.00  0.00           C  
HETATM   21  C15 UNL     1      -5.180   2.418   0.664  1.00  0.00           C  
HETATM   22  C16 UNL     1      -5.235   0.555   2.190  1.00  0.00           C  
HETATM   23  C17 UNL     1      -3.126   0.970   0.911  1.00  0.00           C  
HETATM   24  C18 UNL     1      -2.728   0.006   1.958  1.00  0.00           C  
HETATM   25  C19 UNL     1      -1.285  -0.386   2.054  1.00  0.00           C  
HETATM   26  C20 UNL     1      -0.788  -0.714   0.650  1.00  0.00           C  
HETATM   27  C21 UNL     1      -1.567  -1.939   0.285  1.00  0.00           C  
HETATM   28  C22 UNL     1       0.652  -1.137   0.613  1.00  0.00           C  
HETATM   29  C23 UNL     1       0.902  -2.086  -0.532  1.00  0.00           C  
HETATM   30  C24 UNL     1       1.173  -1.805   1.838  1.00  0.00           C  
HETATM   31  C25 UNL     1       2.682  -1.641   1.597  1.00  0.00           C  
HETATM   32  C26 UNL     1       2.756  -0.138   1.276  1.00  0.00           C  
HETATM   33  C27 UNL     1       4.085   0.295   0.839  1.00  0.00           C  
HETATM   34  C28 UNL     1       4.105   1.793   0.638  1.00  0.00           C  
HETATM   35  C29 UNL     1       5.034   0.056   2.028  1.00  0.00           C  
HETATM   36  C30 UNL     1       6.370   0.169   1.327  1.00  0.00           C  
HETATM   37  C31 UNL     1       6.034  -0.479   0.009  1.00  0.00           C  
HETATM   38  C32 UNL     1       6.890   0.094  -1.050  1.00  0.00           C  
HETATM   39  C33 UNL     1       8.349  -0.106  -0.620  1.00  0.00           C  
HETATM   40  C34 UNL     1       6.754  -0.625  -2.387  1.00  0.00           C  
HETATM   41  O7  UNL     1       6.718   1.432  -1.289  1.00  0.00           O  
HETATM   42  O8  UNL     1       4.687  -0.401  -0.170  1.00  0.00           O  
HETATM   43  C35 UNL     1       1.534   0.117   0.549  1.00  0.00           C  
HETATM   44  H1  UNL     1       3.791  -1.673  -3.242  1.00  0.00           H  
HETATM   45  H2  UNL     1       2.357  -1.240  -4.218  1.00  0.00           H  
HETATM   46  H3  UNL     1       3.970  -0.395  -4.522  1.00  0.00           H  
HETATM   47  H4  UNL     1       1.933   1.586  -0.933  1.00  0.00           H  
HETATM   48  H5  UNL     1      -0.169   1.896  -1.495  1.00  0.00           H  
HETATM   49  H6  UNL     1      -0.310   0.297  -2.164  1.00  0.00           H  
HETATM   50  H7  UNL     1      -0.748   1.411   0.619  1.00  0.00           H  
HETATM   51  H8  UNL     1      -1.476   2.925  -0.369  1.00  0.00           H  
HETATM   52  H9  UNL     1      -2.046   2.358  -2.031  1.00  0.00           H  
HETATM   53  H10 UNL     1      -3.173   2.965  -0.816  1.00  0.00           H  
HETATM   54  H11 UNL     1      -2.804   0.678  -2.523  1.00  0.00           H  
HETATM   55  H12 UNL     1      -2.756  -0.827  -1.671  1.00  0.00           H  
HETATM   56  H13 UNL     1      -4.952  -0.483  -2.180  1.00  0.00           H  
HETATM   57  H14 UNL     1      -4.956   1.273  -1.964  1.00  0.00           H  
HETATM   58  H15 UNL     1      -4.722  -0.950   0.120  1.00  0.00           H  
HETATM   59  H16 UNL     1      -8.835  -2.405  -0.541  1.00  0.00           H  
HETATM   60  H17 UNL     1      -8.912  -1.946   1.166  1.00  0.00           H  
HETATM   61  H18 UNL     1      -9.243   1.709  -0.512  1.00  0.00           H  
HETATM   62  H19 UNL     1      -4.486   3.120   1.163  1.00  0.00           H  
HETATM   63  H20 UNL     1      -5.469   2.676  -0.358  1.00  0.00           H  
HETATM   64  H21 UNL     1      -6.141   2.514   1.252  1.00  0.00           H  
HETATM   65  H22 UNL     1      -4.839   1.095   3.044  1.00  0.00           H  
HETATM   66  H23 UNL     1      -5.295  -0.535   2.262  1.00  0.00           H  
HETATM   67  H24 UNL     1      -6.323   0.879   2.139  1.00  0.00           H  
HETATM   68  H25 UNL     1      -2.864   1.991   1.353  1.00  0.00           H  
HETATM   69  H26 UNL     1      -2.921   0.468   2.982  1.00  0.00           H  
HETATM   70  H27 UNL     1      -3.332  -0.924   2.024  1.00  0.00           H  
HETATM   71  H28 UNL     1      -0.635   0.436   2.473  1.00  0.00           H  
HETATM   72  H29 UNL     1      -1.206  -1.269   2.683  1.00  0.00           H  
HETATM   73  H30 UNL     1      -2.631  -1.926   0.442  1.00  0.00           H  
HETATM   74  H31 UNL     1      -1.204  -2.703   1.055  1.00  0.00           H  
HETATM   75  H32 UNL     1      -1.334  -2.422  -0.657  1.00  0.00           H  
HETATM   76  H33 UNL     1       0.528  -3.097  -0.178  1.00  0.00           H  
HETATM   77  H34 UNL     1       0.394  -1.857  -1.465  1.00  0.00           H  
HETATM   78  H35 UNL     1       1.947  -2.261  -0.778  1.00  0.00           H  
HETATM   79  H36 UNL     1       0.893  -2.870   1.889  1.00  0.00           H  
HETATM   80  H37 UNL     1       0.940  -1.243   2.755  1.00  0.00           H  
HETATM   81  H38 UNL     1       3.152  -1.888   2.569  1.00  0.00           H  
HETATM   82  H39 UNL     1       3.096  -2.286   0.849  1.00  0.00           H  
HETATM   83  H40 UNL     1       2.688   0.294   2.336  1.00  0.00           H  
HETATM   84  H41 UNL     1       4.214   2.136  -0.380  1.00  0.00           H  
HETATM   85  H42 UNL     1       4.873   2.310   1.261  1.00  0.00           H  
HETATM   86  H43 UNL     1       3.132   2.219   1.026  1.00  0.00           H  
HETATM   87  H44 UNL     1       4.889   0.797   2.816  1.00  0.00           H  
HETATM   88  H45 UNL     1       4.954  -0.948   2.430  1.00  0.00           H  
HETATM   89  H46 UNL     1       7.112  -0.406   1.919  1.00  0.00           H  
HETATM   90  H47 UNL     1       6.674   1.213   1.254  1.00  0.00           H  
HETATM   91  H48 UNL     1       6.311  -1.564   0.121  1.00  0.00           H  
HETATM   92  H49 UNL     1       8.708   0.772  -0.045  1.00  0.00           H  
HETATM   93  H50 UNL     1       8.464  -1.031  -0.024  1.00  0.00           H  
HETATM   94  H51 UNL     1       8.985  -0.159  -1.538  1.00  0.00           H  
HETATM   95  H52 UNL     1       7.710  -0.453  -2.927  1.00  0.00           H  
HETATM   96  H53 UNL     1       6.562  -1.694  -2.240  1.00  0.00           H  
HETATM   97  H54 UNL     1       5.977  -0.094  -2.974  1.00  0.00           H  
HETATM   98  H55 UNL     1       7.414   1.964  -0.828  1.00  0.00           H  
HETATM   99  H56 UNL     1       0.957   0.871   1.177  1.00  0.00           H  
CONECT    1    2   44   45   46
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   43   47
CONECT    6    7   48   49
CONECT    7    8   26   50
CONECT    8    9   10   23
CONECT    9   51   52   53
CONECT   10   11   54   55
CONECT   11   12   56   57
CONECT   12   13   20   58
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   59   60
CONECT   17   18   18   19
CONECT   19   61
CONECT   20   21   22   23
CONECT   21   62   63   64
CONECT   22   65   66   67
CONECT   23   24   68
CONECT   24   25   69   70
CONECT   25   26   71   72
CONECT   26   27   28
CONECT   27   73   74   75
CONECT   28   29   30   43
CONECT   29   76   77   78
CONECT   30   31   79   80
CONECT   31   32   81   82
CONECT   32   33   43   83
CONECT   33   34   35   42
CONECT   34   84   85   86
CONECT   35   36   87   88
CONECT   36   37   89   90
CONECT   37   38   42   91
CONECT   38   39   40   41
CONECT   39   92   93   94
CONECT   40   95   96   97
CONECT   41   98
CONECT   43   99
END

HMDB0040498
     RDKit          3D
3-Epipapyriferic acid
 99103  0  0  0  0  0  0  0  0999 V2000
    3.2835   -0.8435   -3.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8545    0.2029   -2.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2854    1.3621   -2.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9543   -0.2100   -1.8414 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    0.5938   -0.8240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0321    0.8064   -1.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9872    0.5357   -0.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4177    0.9296   -0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689    2.3833   -0.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722    0.2230   -1.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5888    0.3525   -1.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1332    0.0408   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5348   -0.0907   -0.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1273   -1.2937    0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3639   -2.2574    0.3898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5777   -1.5689    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3763   -0.3680   -0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6223   -0.4089   -0.1904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7321    0.8284   -0.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6324    1.0276    0.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1795    2.4180    0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2351    0.5553    2.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1262    0.9700    0.9106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7278    0.0056    1.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2853   -0.3861    2.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883   -0.7137    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5668   -1.9386    0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6522   -1.1374    0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9020   -2.0857   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734   -1.8052    1.8379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6817   -1.6410    1.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7561   -0.1382    1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0848    0.2954    0.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1055    1.7931    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0344    0.0561    2.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3703    0.1693    1.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0341   -0.4787    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8903    0.0944   -1.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3488   -0.1057   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7540   -0.6252   -2.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7182    1.4320   -1.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6869   -0.4008   -0.1696 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335    0.1168    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7911   -1.6727   -3.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9699   -0.3954   -4.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9325    1.5857   -0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7483    1.4114    0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763    2.9248   -0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0456    2.3583   -2.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1730    2.9651   -0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8041    0.6782   -2.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7564   -0.8270   -1.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.8349   -2.4049   -0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.2431    1.7087   -0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4863    3.1203    1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4685    2.6758   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1407    2.5136    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8390    1.0946    3.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2946   -0.5352    2.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3232    0.8790    2.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8644    1.9912    1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9212    0.4683    2.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3320   -0.9239    2.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354    0.4363    2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6312   -1.9256    0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039   -2.7033    1.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3344   -2.4216   -0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5284   -3.0972   -0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3937   -1.8571   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466   -2.2614   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933   -2.8697    1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404   -1.2428    2.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1517   -1.8875    2.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962   -2.2857    0.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875    0.2937    2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141    2.1363   -0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8730    2.3105    1.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1322    2.2186    1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8891    0.7971    2.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9540   -0.9483    2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1117   -0.4064    1.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    1.2132    1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3109   -1.5643    0.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7084    0.7723   -0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4641   -1.0307   -0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9846   -0.1595   -1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7100   -0.4532   -2.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5617   -1.6942   -2.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9771   -0.0935   -2.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4143    1.9645   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9567    0.8710    1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Epipapyriferate	Generator
[2,2']Bi[1,3,4,9-tetrathia-cyclopenta[b]naphthalenylidene]	HMDB
3-{[16-(acetyloxy)-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-oxopropanoate	Generator

Chemical Formula

C₃₅H₅₆O₈

Average Molecular Weight

604.8143

Monoisotopic Molecular Weight

604.397518768

IUPAC Name

3-{[16-(acetyloxy)-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-oxopropanoic acid

Traditional Name

3-{[16-(acetyloxy)-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-oxopropanoic acid

CAS Registry Number

151890-02-7

SMILES

CC(=O)OC1CC2C3(C)CCC(OC(=O)CC(O)=O)C(C)(C)C3CCC2(C)C2(C)CCC(C12)C1(C)CCC(O1)C(C)(C)O

InChI Identifier

InChI=1S/C35H56O8/c1-20(36)41-22-18-24-32(6)14-12-25(42-28(39)19-27(37)38)30(2,3)23(32)11-16-33(24,7)34(8)15-10-21(29(22)34)35(9)17-13-26(43-35)31(4,5)40/h21-26,29,40H,10-19H2,1-9H3,(H,37,38)

InChI Key

RLVAVWQAAQFUOP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Steroid ester
Steroid
Tricarboxylic acid or derivatives
1,3-dicarbonyl compound
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0040498)
Cell membrane (HMDB: HMDB0040498)

Cellular substructure

Extracellular (HMDB: HMDB0040498)
Membrane (HMDB: HMDB0040498)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040498)

Source

Endogenous

Endogenous (HMDB: HMDB0040498)

Animal

Animal (HMDB: HMDB0040498)

Exogenous

Food

Food (HMDB: HMDB0040498)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0040498)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0040498)

Cellular process

Cell signaling (HMDB: HMDB0040498)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0040498)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0040498)

Nutrient

Nutrient (HMDB: HMDB0040498)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040498)

Emulsifier (HMDB: HMDB0040498)

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	0.00031 g/L	ALOGPS
logP	5.82	ALOGPS
logP	5.33	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	160.72 m³·mol⁻¹	ChemAxon
Polarizability	68.43 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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]+	236.069	31661259
DarkChem	[M-H]-	227.335	31661259
DeepCCS	[M-2H]-	279.908	30932474
DeepCCS	[M+Na]+	254.791	30932474
AllCCS	[M+H]+	241.6	32859911
AllCCS	[M+H-H2O]+	240.6	32859911
AllCCS	[M+NH4]+	242.4	32859911
AllCCS	[M+Na]+	242.6	32859911
AllCCS	[M-H]-	229.2	32859911
AllCCS	[M+Na-2H]-	233.4	32859911
AllCCS	[M+HCOO]-	238.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Epipapyriferic acid	CC(=O)OC1CC2C3(C)CCC(OC(=O)CC(O)=O)C(C)(C)C3CCC2(C)C2(C)CCC(C12)C1(C)CCC(O1)C(C)(C)O	4225.4	Standard polar	33892256
3-Epipapyriferic acid	CC(=O)OC1CC2C3(C)CCC(OC(=O)CC(O)=O)C(C)(C)C3CCC2(C)C2(C)CCC(C12)C1(C)CCC(O1)C(C)(C)O	3702.6	Standard non polar	33892256
3-Epipapyriferic acid	CC(=O)OC1CC2C3(C)CCC(OC(=O)CC(O)=O)C(C)(C)C3CCC2(C)C2(C)CCC(C12)C1(C)CCC(O1)C(C)(C)O	4249.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Epipapyriferic acid,1TMS,isomer #1	CC(=O)OC1CC2C3(C)CCC(OC(=O)CC(=O)O[Si](C)(C)C)C(C)(C)C3CCC2(C)C2(C)CCC(C3(C)CCC(C(C)(C)O)O3)C12	4125.1	Semi standard non polar	33892256
3-Epipapyriferic acid,1TMS,isomer #2	CC(=O)OC1CC2C3(C)CCC(OC(=O)CC(=O)O)C(C)(C)C3CCC2(C)C2(C)CCC(C3(C)CCC(C(C)(C)O[Si](C)(C)C)O3)C12	4248.7	Semi standard non polar	33892256
3-Epipapyriferic acid,2TMS,isomer #1	CC(=O)OC1CC2C3(C)CCC(OC(=O)CC(=O)O[Si](C)(C)C)C(C)(C)C3CCC2(C)C2(C)CCC(C3(C)CCC(C(C)(C)O[Si](C)(C)C)O3)C12	4168.8	Semi standard non polar	33892256
3-Epipapyriferic acid,1TBDMS,isomer #1	CC(=O)OC1CC2C3(C)CCC(OC(=O)CC(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)C3CCC2(C)C2(C)CCC(C3(C)CCC(C(C)(C)O)O3)C12	4322.9	Semi standard non polar	33892256
3-Epipapyriferic acid,1TBDMS,isomer #2	CC(=O)OC1CC2C3(C)CCC(OC(=O)CC(=O)O)C(C)(C)C3CCC2(C)C2(C)CCC(C3(C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)O3)C12	4448.5	Semi standard non polar	33892256
3-Epipapyriferic acid,2TBDMS,isomer #1	CC(=O)OC1CC2C3(C)CCC(OC(=O)CC(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)C3CCC2(C)C2(C)CCC(C3(C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)O3)C12	4551.5	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-Epipapyriferic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4v-6010390000-4023dc45242f18d89d96	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epipapyriferic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epipapyriferic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epipapyriferic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epipapyriferic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epipapyriferic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epipapyriferic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epipapyriferic acid GC-MS ("3-Epipapyriferic acid,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-20	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 - 3-Epipapyriferic acid 10V, Positive-QTOF	splash10-05n0-2000091000-27931f6969cbaf5d68d8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epipapyriferic acid 20V, Positive-QTOF	splash10-0frm-4000290000-d2905cec0443fe002b5e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epipapyriferic acid 40V, Positive-QTOF	splash10-0kbv-4010950000-870f8247b3df77f2878a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epipapyriferic acid 10V, Negative-QTOF	splash10-1003-1000093000-e932f43e983f684d6350	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epipapyriferic acid 20V, Negative-QTOF	splash10-0aou-3000290000-1356a0549d0fd0b6995a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epipapyriferic acid 40V, Negative-QTOF	splash10-059x-9000850000-536d961bab08e274c18d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epipapyriferic acid 10V, Positive-QTOF	splash10-0zfs-0001795000-3b3ef989b8b9025e04cf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epipapyriferic acid 20V, Positive-QTOF	splash10-0ldr-2152791000-cb977fcf5ca462d39db3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epipapyriferic acid 40V, Positive-QTOF	splash10-0a7j-9135300000-ac8a919d46b81d3b9251	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epipapyriferic acid 10V, Negative-QTOF	splash10-0pba-9200821000-1d2b2572b838441dd5f2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epipapyriferic acid 20V, Negative-QTOF	splash10-0a4i-9000200000-cb46a9707e92c2b52ffb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epipapyriferic acid 40V, Negative-QTOF	splash10-0a4i-9000011000-4d9e0ce9c681e46de5ff	2021-09-23	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

FDB020261

KNApSAcK ID

Not Available

Chemspider ID

511579

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

588518

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 3-Epipapyriferic acid (HMDB0040498)

MOL for HMDB0040498 (3-Epipapyriferic acid)

3D MOL for HMDB0040498 (3-Epipapyriferic acid)

3D SDF for HMDB0040498 (3-Epipapyriferic acid)

3D-SDF for HMDB0040498 (3-Epipapyriferic acid)

PDB for HMDB0040498 (3-Epipapyriferic acid)

3D PDB for HMDB0040498 (3-Epipapyriferic acid)

SMILES for HMDB0040498 (3-Epipapyriferic acid)

INCHI for HMDB0040498 (3-Epipapyriferic acid)

Structure for HMDB0040498 (3-Epipapyriferic acid)

3D Structure for HMDB0040498 (3-Epipapyriferic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra