NP-MRD: Showing NP-Card for Uvaol (NP0001372)

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Record Information

Version

2.0

Created at

2006-05-22 14:17:51 UTC

Updated at

2024-09-17 15:45:00 UTC

NP-MRD ID

NP0001372

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Uvaol

Description

Uvaol is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Uvaol exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. (PMID: 17292619 ).

Structure

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


  Mrv1652305012020112D          

 35 39  0  0  0  0            999 V2000
   18.4400   -8.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4275   -9.0708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.7191   -9.4791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1524   -7.8293    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2901   -9.4832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.8648   -8.2541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0025   -9.0666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2944  -10.3081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.7191   -7.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5778  -10.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5772   -8.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1649   -6.9960    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.1399   -9.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7191  -10.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0025   -8.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8648   -9.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5778   -9.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0025  -10.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5897   -7.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8695  -10.3081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.8898   -6.5918    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8695   -9.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6022   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4275   -9.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7150   -8.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2901   -8.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1569  -11.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9818  -11.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4442   -6.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9023   -5.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1524   -8.6542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.0025   -9.8915    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.2901  -11.1289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1552  -10.7209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5763   -9.4916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  7  1  0  0  0  0
  6  4  1  0  0  0  0
  7 15  1  0  0  0  0
  8  5  1  0  0  0  0
  9  1  2  0  0  0  0
 10  8  1  0  0  0  0
  6 11  1  1  0  0  0
 12  4  1  0  0  0  0
 13  2  1  0  0  0  0
 14  3  1  0  0  0  0
 15  9  1  0  0  0  0
 16  6  1  0  0  0  0
 17  5  1  0  0  0  0
 18 14  1  0  0  0  0
 19  6  1  0  0  0  0
 20 22  1  0  0  0  0
 21 12  1  0  0  0  0
 22 17  1  0  0  0  0
 23 21  1  0  0  0  0
  2 24  1  6  0  0  0
  3 25  1  1  0  0  0
  5 26  1  1  0  0  0
 27 10  1  0  0  0  0
 28 10  1  0  0  0  0
 12 29  1  1  0  0  0
 21 30  1  6  0  0  0
  4 31  1  1  0  0  0
  7 32  1  6  0  0  0
  8 33  1  6  0  0  0
  3  7  1  0  0  0  0
 13 16  1  0  0  0  0
 19 23  1  0  0  0  0
  8 18  1  0  0  0  0
 10 20  1  0  0  0  0
 20 34  1  1  0  0  0
  2  1  1  0  0  0  0
 11 35  1  0  0  0  0
M  END

HMDB0002391
     RDKit          3D
Uvaol
 82 86  0  0  0  0  0  0  0  0999 V2000
   -3.8351   -2.3886   -0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8321   -0.8623   -0.6175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9550   -0.2268    0.4263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5434   -0.1823   -0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3190   -1.0021   -1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2560   -0.2884   -0.6438 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6816   -0.8204   -0.6498 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8261   -2.2416   -0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1779   -0.6891   -2.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6757   -0.7167   -2.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2725    0.3812   -1.3620 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6261    0.5556   -1.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226    0.1477    0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4017    1.4122    0.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4427    0.1434    0.2120 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9648    0.0583    1.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5753    0.7088    1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6895   -0.0392    0.6924 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2991   -1.3129    1.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5780    0.8189    0.4699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2437    1.9315   -0.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420    1.3536    1.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4450    2.0324    1.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4690    1.0341    1.0036 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -4.8106    1.9295    2.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741    1.7862    0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7793   -2.6981    0.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7990   -2.9353   -1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0346   -2.6805    0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4773   -0.6427   -1.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001   -0.9698    1.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236   -1.7514   -1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6387   -2.0282   -1.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6501   -2.4930    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2639   -2.8755   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9029   -2.5235   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7685    0.1874   -2.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8034   -1.5858   -2.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0946   -1.7111   -1.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244   -0.5205   -3.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462    1.3324   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8307    1.5234   -1.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0985   -1.6440   -0.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0370   -1.5929    1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5348   -0.6631    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3827    1.7454    0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5700    1.1061    1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6248    2.1838    0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225    1.1702   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9635   -0.9424    2.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5878    0.7120    2.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1942    0.5766    2.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6889    1.7716    1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299   -2.1827    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0136   -1.5169    2.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7726    2.3831   -0.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    1.6408   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4334    2.8664    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7484    2.5004    2.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3635   -0.3864   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
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 22 23  1  6
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 29 30  1  0
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 31 32  1  0
 31  2  1  0
 26  3  1  0
 22  4  1  0
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  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  6
  3 37  1  1
  5 38  1  0
  6 39  1  0
  6 40  1  0
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 16 55  1  0
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 17 57  1  6
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 21 62  1  0
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 27 72  1  0
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 29 75  1  0
 29 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  1
 32 80  1  0
 32 81  1  0
 32 82  1  0
M  END


  Mrv1652305012020112D          

 35 39  0  0  0  0            999 V2000
   18.4400   -8.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4275   -9.0708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.7191   -9.4791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1524   -7.8293    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2901   -9.4832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.8648   -8.2541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0025   -9.0666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2944  -10.3081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.7191   -7.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5778  -10.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5772   -8.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1649   -6.9960    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.1399   -9.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7191  -10.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0025   -8.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8648   -9.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5778   -9.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0025  -10.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5897   -7.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8695  -10.3081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.8898   -6.5918    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8695   -9.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6022   -7.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4275   -9.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7150   -8.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.4442   -6.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9023   -5.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1524   -8.6542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.0025   -9.8915    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.2901  -11.1289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1552  -10.7209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5763   -9.4916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  7  1  0  0  0  0
  6  4  1  0  0  0  0
  7 15  1  0  0  0  0
  8  5  1  0  0  0  0
  9  1  2  0  0  0  0
 10  8  1  0  0  0  0
  6 11  1  1  0  0  0
 12  4  1  0  0  0  0
 13  2  1  0  0  0  0
 14  3  1  0  0  0  0
 15  9  1  0  0  0  0
 16  6  1  0  0  0  0
 17  5  1  0  0  0  0
 18 14  1  0  0  0  0
 19  6  1  0  0  0  0
 20 22  1  0  0  0  0
 21 12  1  0  0  0  0
 22 17  1  0  0  0  0
 23 21  1  0  0  0  0
  2 24  1  6  0  0  0
  3 25  1  1  0  0  0
  5 26  1  1  0  0  0
 27 10  1  0  0  0  0
 28 10  1  0  0  0  0
 12 29  1  1  0  0  0
 21 30  1  6  0  0  0
  4 31  1  1  0  0  0
  7 32  1  6  0  0  0
  8 33  1  6  0  0  0
  3  7  1  0  0  0  0
 13 16  1  0  0  0  0
 19 23  1  0  0  0  0
  8 18  1  0  0  0  0
 10 20  1  0  0  0  0
 20 34  1  1  0  0  0
  2  1  1  0  0  0  0
 11 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001372

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@@H](C)[C@H](C)CC[C@]1(CO)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O2/c1-19-10-15-30(18-31)17-16-28(6)21(25(30)20(19)2)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h8,19-20,22-25,31-32H,9-18H2,1-7H3/t19-,20+,22+,23-,24+,25+,27+,28-,29-,30-/m1/s1

> <INCHI_KEY>
XUARCIYIVXVTAE-ZAPOICBTSA-N

> <FORMULA>
C30H50O2

> <MOLECULAR_WEIGHT>
442.728

> <EXACT_MASS>
442.38108085

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
54.679501090128895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-ol

> <ALOGPS_LOGP>
6.13

> <JCHEM_LOGP>
6.109341654000001

> <ALOGPS_LOGS>
-6.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.489433291560097

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.953297110466607

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6357052290198816

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
133.75549999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.72e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
uvaol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002391
     RDKit          3D
Uvaol
 82 86  0  0  0  0  0  0  0  0999 V2000
   -3.8351   -2.3886   -0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8321   -0.8623   -0.6175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9550   -0.2268    0.4263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5434   -0.1823   -0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0599   -0.9937   -0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3190   -1.0021   -1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2560   -0.2884   -0.6438 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6816   -0.8204   -0.6498 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8261   -2.2416   -0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1779   -0.6891   -2.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6757   -0.7167   -2.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2725    0.3812   -1.3620 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6261    0.5556   -1.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226    0.1477    0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6331   -1.0029    0.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4017    1.4122    0.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4427    0.1434    0.2120 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9648    0.0583    1.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5753    0.7088    1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6895   -0.0392    0.6924 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2991   -1.3129    1.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5780    0.8189    0.4699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2437    1.9315   -0.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420    1.3536    1.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4450    2.0324    1.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4690    1.0341    1.0036 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3313    0.7571    2.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8106    1.9295    2.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741    1.7862    0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5471    0.9723   -0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2772   -0.4684   -0.5857 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8719   -0.8867   -1.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7793   -2.6981    0.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7990   -2.9353   -1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0346   -2.6805    0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4773   -0.6427   -1.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001   -0.9698    1.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236   -1.7514   -1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6387   -2.0282   -1.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2527   -0.4665   -2.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080    0.7260   -1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6501   -2.4930    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2639   -2.8755   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9029   -2.5235   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7685    0.1874   -2.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8034   -1.5858   -2.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0946   -1.7111   -1.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244   -0.5205   -3.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462    1.3324   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8307    1.5234   -1.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0985   -1.6440   -0.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0370   -1.5929    1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5348   -0.6631    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3827    1.7454    0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5700    1.1061    1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6248    2.1838    0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225    1.1702   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9635   -0.9424    2.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5878    0.7120    2.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1942    0.5766    2.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6889    1.7716    1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299   -2.1827    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0136   -1.5169    2.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6933   -1.2230    1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726    2.3831   -0.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    1.6408   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8858    2.8317   -0.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116    0.6125    2.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4014    2.0848    2.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4334    2.8664    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7484    2.5004    2.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0907   -0.0145    2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6679    0.3047    3.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5580    2.2932    2.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6222    2.7337    0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7136    2.0128   -0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9375    1.4050   -1.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3814    1.1553    0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8657   -1.0985    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7850   -1.9868   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9496   -0.6271   -1.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3635   -0.3864   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 27 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31  2  1  0
 26  3  1  0
 22  4  1  0
 20  7  1  0
 17  8  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  6
  3 37  1  1
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  6
  9 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  6
 13 50  1  0
 15 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  6
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 21 62  1  0
 21 63  1  0
 21 64  1  0
 23 65  1  0
 23 66  1  0
 23 67  1  0
 24 68  1  0
 24 69  1  0
 25 70  1  0
 25 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
 29 75  1  0
 29 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  1
 32 80  1  0
 32 81  1  0
 32 82  1  0
M  END

HEADER    PROTEIN                                 01-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-20         0                                  
HETATM    1  C   UNK     0      34.421 -15.384   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.398 -16.932   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.076 -17.694   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      35.751 -14.615   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.408 -17.702   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      37.081 -15.408   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.738 -16.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.416 -19.242   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.076 -14.599   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.079 -20.004   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      38.411 -16.178   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.774 -13.059   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.728 -17.702   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.076 -19.234   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.738 -15.369   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.081 -16.947   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.079 -16.924   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.738 -20.004   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      38.434 -14.646   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.756 -19.242   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      37.128 -12.305   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.756 -17.702   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      38.457 -13.106   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      34.398 -18.472   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      33.068 -16.154   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      30.408 -16.162   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      28.293 -21.334   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.833 -21.334   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      34.429 -12.266   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      37.151 -10.765   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0      35.751 -16.154   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      31.738 -18.464   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      30.408 -20.774   0.000  0.00  0.00           H+0
HETATM   34  O   UNK     0      26.423 -20.012   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      38.409 -17.718   0.000  0.00  0.00           O+0
CONECT    1    4    9    2                                                  
CONECT    2    3   13   24    1                                             
CONECT    3    2   14   25    7                                             
CONECT    4    1    6   12   31                                             
CONECT    5    7    8   17   26                                             
CONECT    6    4   11   16   19                                             
CONECT    7    5   15   32    3                                             
CONECT    8    5   10   33   18                                             
CONECT    9    1   15                                                       
CONECT   10    8   27   28   20                                             
CONECT   11    6   35                                                       
CONECT   12    4   21   29                                                  
CONECT   13    2   16                                                       
CONECT   14    3   18                                                       
CONECT   15    7    9                                                       
CONECT   16    6   13                                                       
CONECT   17    5   22                                                       
CONECT   18   14    8                                                       
CONECT   19    6   23                                                       
CONECT   20   22   10   34                                                  
CONECT   21   12   23   30                                                  
CONECT   22   20   17                                                       
CONECT   23   21   19                                                       
CONECT   24    2                                                            
CONECT   25    3                                                            
CONECT   26    5                                                            
CONECT   27   10                                                            
CONECT   28   10                                                            
CONECT   29   12                                                            
CONECT   30   21                                                            
CONECT   31    4                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34   20                                                            
CONECT   35   11                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

COMPND    HMDB0002391
HETATM    1  C1  UNL     1      -3.835  -2.389  -0.389  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.832  -0.862  -0.617  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.955  -0.227   0.426  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.543  -0.182  -0.075  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.060  -0.994  -0.988  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.319  -1.002  -1.521  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.256  -0.288  -0.644  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.682  -0.820  -0.650  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.826  -2.242  -0.275  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.178  -0.689  -2.074  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.676  -0.717  -2.179  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.272   0.381  -1.362  1.00  0.00           C  
HETATM   13  O1  UNL     1       6.626   0.556  -1.571  1.00  0.00           O  
HETATM   14  C13 UNL     1       4.923   0.148   0.081  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.633  -1.003   0.701  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.402   1.412   0.822  1.00  0.00           C  
HETATM   17  C16 UNL     1       3.443   0.143   0.212  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.965   0.058   1.637  1.00  0.00           C  
HETATM   19  C18 UNL     1       1.575   0.709   1.645  1.00  0.00           C  
HETATM   20  C19 UNL     1       0.689  -0.039   0.692  1.00  0.00           C  
HETATM   21  C20 UNL     1       0.299  -1.313   1.405  1.00  0.00           C  
HETATM   22  C21 UNL     1      -0.578   0.819   0.470  1.00  0.00           C  
HETATM   23  C22 UNL     1      -0.244   1.931  -0.461  1.00  0.00           C  
HETATM   24  C23 UNL     1      -1.142   1.354   1.717  1.00  0.00           C  
HETATM   25  C24 UNL     1      -2.445   2.032   1.469  1.00  0.00           C  
HETATM   26  C25 UNL     1      -3.469   1.034   1.004  1.00  0.00           C  
HETATM   27  C26 UNL     1      -4.331   0.757   2.261  1.00  0.00           C  
HETATM   28  O2  UNL     1      -4.811   1.930   2.799  1.00  0.00           O  
HETATM   29  C27 UNL     1      -4.374   1.786   0.010  1.00  0.00           C  
HETATM   30  C28 UNL     1      -5.547   0.972  -0.394  1.00  0.00           C  
HETATM   31  C29 UNL     1      -5.277  -0.468  -0.586  1.00  0.00           C  
HETATM   32  C30 UNL     1      -5.872  -0.887  -1.946  1.00  0.00           C  
HETATM   33  H1  UNL     1      -4.779  -2.698   0.113  1.00  0.00           H  
HETATM   34  H2  UNL     1      -3.799  -2.935  -1.337  1.00  0.00           H  
HETATM   35  H3  UNL     1      -3.035  -2.681   0.338  1.00  0.00           H  
HETATM   36  H4  UNL     1      -3.477  -0.643  -1.652  1.00  0.00           H  
HETATM   37  H5  UNL     1      -3.000  -0.970   1.302  1.00  0.00           H  
HETATM   38  H6  UNL     1      -1.724  -1.751  -1.421  1.00  0.00           H  
HETATM   39  H7  UNL     1       0.639  -2.028  -1.819  1.00  0.00           H  
HETATM   40  H8  UNL     1       0.253  -0.466  -2.517  1.00  0.00           H  
HETATM   41  H9  UNL     1       1.408   0.726  -1.130  1.00  0.00           H  
HETATM   42  H10 UNL     1       2.650  -2.493   0.778  1.00  0.00           H  
HETATM   43  H11 UNL     1       2.264  -2.875  -0.981  1.00  0.00           H  
HETATM   44  H12 UNL     1       3.903  -2.523  -0.478  1.00  0.00           H  
HETATM   45  H13 UNL     1       2.768   0.187  -2.596  1.00  0.00           H  
HETATM   46  H14 UNL     1       2.803  -1.586  -2.642  1.00  0.00           H  
HETATM   47  H15 UNL     1       5.095  -1.711  -1.934  1.00  0.00           H  
HETATM   48  H16 UNL     1       4.924  -0.521  -3.242  1.00  0.00           H  
HETATM   49  H17 UNL     1       4.746   1.332  -1.661  1.00  0.00           H  
HETATM   50  H18 UNL     1       6.831   1.523  -1.529  1.00  0.00           H  
HETATM   51  H19 UNL     1       6.098  -1.644  -0.106  1.00  0.00           H  
HETATM   52  H20 UNL     1       5.037  -1.593   1.416  1.00  0.00           H  
HETATM   53  H21 UNL     1       6.535  -0.663   1.295  1.00  0.00           H  
HETATM   54  H22 UNL     1       6.383   1.745   0.448  1.00  0.00           H  
HETATM   55  H23 UNL     1       5.570   1.106   1.887  1.00  0.00           H  
HETATM   56  H24 UNL     1       4.625   2.184   0.831  1.00  0.00           H  
HETATM   57  H25 UNL     1       3.122   1.170  -0.151  1.00  0.00           H  
HETATM   58  H26 UNL     1       2.964  -0.942   2.063  1.00  0.00           H  
HETATM   59  H27 UNL     1       3.588   0.712   2.295  1.00  0.00           H  
HETATM   60  H28 UNL     1       1.194   0.577   2.682  1.00  0.00           H  
HETATM   61  H29 UNL     1       1.689   1.772   1.463  1.00  0.00           H  
HETATM   62  H30 UNL     1       0.230  -2.183   0.732  1.00  0.00           H  
HETATM   63  H31 UNL     1       1.014  -1.517   2.227  1.00  0.00           H  
HETATM   64  H32 UNL     1      -0.693  -1.223   1.893  1.00  0.00           H  
HETATM   65  H33 UNL     1       0.773   2.383  -0.243  1.00  0.00           H  
HETATM   66  H34 UNL     1      -0.330   1.641  -1.552  1.00  0.00           H  
HETATM   67  H35 UNL     1      -0.886   2.832  -0.401  1.00  0.00           H  
HETATM   68  H36 UNL     1      -1.312   0.613   2.522  1.00  0.00           H  
HETATM   69  H37 UNL     1      -0.401   2.085   2.161  1.00  0.00           H  
HETATM   70  H38 UNL     1      -2.433   2.866   0.746  1.00  0.00           H  
HETATM   71  H39 UNL     1      -2.748   2.500   2.451  1.00  0.00           H  
HETATM   72  H40 UNL     1      -5.091  -0.015   2.062  1.00  0.00           H  
HETATM   73  H41 UNL     1      -3.668   0.305   3.056  1.00  0.00           H  
HETATM   74  H42 UNL     1      -5.558   2.293   2.263  1.00  0.00           H  
HETATM   75  H43 UNL     1      -4.622   2.734   0.504  1.00  0.00           H  
HETATM   76  H44 UNL     1      -3.714   2.013  -0.868  1.00  0.00           H  
HETATM   77  H45 UNL     1      -5.938   1.405  -1.364  1.00  0.00           H  
HETATM   78  H46 UNL     1      -6.381   1.155   0.323  1.00  0.00           H  
HETATM   79  H47 UNL     1      -5.866  -1.098   0.137  1.00  0.00           H  
HETATM   80  H48 UNL     1      -5.785  -1.987  -1.970  1.00  0.00           H  
HETATM   81  H49 UNL     1      -6.950  -0.627  -1.893  1.00  0.00           H  
HETATM   82  H50 UNL     1      -5.364  -0.386  -2.773  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3   31   36
CONECT    3    4   26   37
CONECT    4    5    5   22
CONECT    5    6   38
CONECT    6    7   39   40
CONECT    7    8   20   41
CONECT    8    9   10   17
CONECT    9   42   43   44
CONECT   10   11   45   46
CONECT   11   12   47   48
CONECT   12   13   14   49
CONECT   13   50
CONECT   14   15   16   17
CONECT   15   51   52   53
CONECT   16   54   55   56
CONECT   17   18   57
CONECT   18   19   58   59
CONECT   19   20   60   61
CONECT   20   21   22
CONECT   21   62   63   64
CONECT   22   23   24
CONECT   23   65   66   67
CONECT   24   25   68   69
CONECT   25   26   70   71
CONECT   26   27   29
CONECT   27   28   72   73
CONECT   28   74
CONECT   29   30   75   76
CONECT   30   31   77   78
CONECT   31   32   79
CONECT   32   80   81   82
END

HMDB0002391
     RDKit          3D
Uvaol
 82 86  0  0  0  0  0  0  0  0999 V2000
   -3.8351   -2.3886   -0.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8321   -0.8623   -0.6175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9550   -0.2268    0.4263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5434   -0.1823   -0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0599   -0.9937   -0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3190   -1.0021   -1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2560   -0.2884   -0.6438 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6816   -0.8204   -0.6498 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8261   -2.2416   -0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1779   -0.6891   -2.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6757   -0.7167   -2.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2725    0.3812   -1.3620 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6261    0.5556   -1.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226    0.1477    0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6331   -1.0029    0.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4017    1.4122    0.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4427    0.1434    0.2120 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9648    0.0583    1.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5753    0.7088    1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6895   -0.0392    0.6924 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2991   -1.3129    1.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5780    0.8189    0.4699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2437    1.9315   -0.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420    1.3536    1.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4450    2.0324    1.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4690    1.0341    1.0036 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3313    0.7571    2.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8106    1.9295    2.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741    1.7862    0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5471    0.9723   -0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2772   -0.4684   -0.5857 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8719   -0.8867   -1.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7793   -2.6981    0.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7990   -2.9353   -1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0346   -2.6805    0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4773   -0.6427   -1.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001   -0.9698    1.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236   -1.7514   -1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6387   -2.0282   -1.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2527   -0.4665   -2.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080    0.7260   -1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6501   -2.4930    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2639   -2.8755   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9029   -2.5235   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7685    0.1874   -2.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8034   -1.5858   -2.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0946   -1.7111   -1.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244   -0.5205   -3.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462    1.3324   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8307    1.5234   -1.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0985   -1.6440   -0.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0370   -1.5929    1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5348   -0.6631    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3827    1.7454    0.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5700    1.1061    1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6248    2.1838    0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225    1.1702   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9635   -0.9424    2.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5878    0.7120    2.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1942    0.5766    2.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6889    1.7716    1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299   -2.1827    0.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0136   -1.5169    2.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6933   -1.2230    1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7726    2.3831   -0.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    1.6408   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8858    2.8317   -0.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116    0.6125    2.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4014    2.0848    2.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4334    2.8664    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7484    2.5004    2.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0907   -0.0145    2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6679    0.3047    3.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5580    2.2932    2.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6222    2.7337    0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7136    2.0128   -0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9375    1.4050   -1.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3814    1.1553    0.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8657   -1.0985    0.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7850   -1.9868   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9496   -0.6271   -1.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3635   -0.3864   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 27 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31  2  1  0
 26  3  1  0
 22  4  1  0
 20  7  1  0
 17  8  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  6
  3 37  1  1
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  6
  9 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  6
 13 50  1  0
 15 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  6
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 21 62  1  0
 21 63  1  0
 21 64  1  0
 23 65  1  0
 23 66  1  0
 23 67  1  0
 24 68  1  0
 24 69  1  0
 25 70  1  0
 25 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
 29 75  1  0
 29 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  1
 32 80  1  0
 32 81  1  0
 32 82  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3.beta.)-urs-12-ene-3,28-diol	HMDB
(3beta)-Urs-12-ene-3,28-diol	HMDB
Urs-12-ene-3,28-diol	HMDB
Urs-12-ene-3beta,28-diol	HMDB
Urs-12-ene-3 beta,28-diol	HMDB
Uvaol	MeSH

Chemical Formula

C₃₀H₅₀O₂

Average Mass

442.7280 Da

Monoisotopic Mass

442.38108 Da

IUPAC Name

(3S,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-ol

Traditional Name

uvaol

CAS Registry Number

545-46-0

SMILES

[H]OC([H])([H])[C@]12C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@]([H])(C([H])([H])[H])[C@@]1([H])C1=C([H])C([H])([H])[C@]3([H])[C@@]4(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(O[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]4([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]1(C([H])([H])[H])C([H])([H])C2([H])[H]

InChI Identifier

InChI=1S/C30H50O2/c1-19-10-15-30(18-31)17-16-28(6)21(25(30)20(19)2)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h8,19-20,22-25,31-32H,9-18H2,1-7H3/t19-,20+,22+,23-,24+,25+,27+,28-,29-,30-/m1/s1

InChI Key

XUARCIYIVXVTAE-ZAPOICBTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alibertia edulis	LOTUS Database	35616633
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Arctostaphylos patula	LOTUS Database	35616633
Baccharis coridifolia	LOTUS Database	35616633
Baccharis dracunculifolia	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Callistemon lanceolatus	LOTUS Database	35616633
Calluna vulgaris	LOTUS Database	35616633
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Crataegus pinnatifida	LOTUS Database	35616633
Cydonia oblonga	LOTUS Database	35616633
Cylicodiscus gabunensis	LOTUS Database	35616633
Diospyros kaki	KNApSAcK Database	22123792
Diospyros lotus	KNApSAcK Database	22123792
Diospyros maingayi	KNApSAcK Database	22123792
Diospyros melanoxylon	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Empetrum nigrum	LOTUS Database	35616633
Englerophytum magalismontanum	LOTUS Database	35616633
Equus caballus	FooDB	FooDB
Eriobotrya japonica	LOTUS Database	35616633
Eucalyptus globulus	LOTUS Database	35616633
Eucalyptus robusta	LOTUS Database	35616633
Eucalyptus saligna	LOTUS Database	35616633
Euonymus alatus	LOTUS Database	35616633
Euphorbia micractina	KNApSAcK Database	22123792
Euphorbia paralias	KNApSAcK Database	22123792
Euphorbia retusa	LOTUS Database	35616633
Gallus gallus	FooDB	FooDB
Hex aquifolium	-	KNApSAcK
Hippophae rhamnoides	LOTUS Database	35616633
Ilex buxifolia	LOTUS Database	35616633
Ilex latifolia	KNApSAcK Database	22123792
Isodon coetsa	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Lecanthus peduncularis	LOTUS Database	35616633
Leporidae	FooDB	FooDB
Leptospermum scoparium	LOTUS Database	35616633
Lepus timidus	FooDB	FooDB
Leucothoe keiskei	LOTUS Database	35616633
Licania pyrifolia	LOTUS Database	35616633
Maclura pomifera	LOTUS Database	35616633
Malus pumila	FooDB	16448186
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Microtropis fokienensis	KNApSAcK Database	22123792
Morus alba	LOTUS Database	35616633
Nerium oleander	KNApSAcK Database	22123792
Nierembergia hippomanica	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Nuxia sphaerocephala	KNApSAcK Database	22123792
Ocimum basilicum	KNApSAcK Database	22123792
Odocoileus	FooDB	FooDB
Olea europaea	KNApSAcK Database	22123792
Origanum dictamnus	LOTUS Database	35616633
Origanum pampaninii	Plant	KNApSAcK
Oryctolagus	FooDB	FooDB
Osmanthus fragrans	KNApSAcK Database	22123792
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Prunus avium	KNApSAcK Database	22123792
Prunus serotina	KNApSAcK Database	22123792
Psidium guajava	LOTUS Database	35616633
Pyracantha coccinea	LOTUS Database	35616633
Rhododendron ferrugineum	LOTUS Database	35616633
Rhododendron moulmainense	LOTUS Database	35616633
Rubus idaeus	LOTUS Database	35616633
Salacia chinensis	LOTUS Database	35616633
Salvia lanata	LOTUS Database	35616633
Salvia officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia tomentosa	LOTUS Database	35616633
Shorea robusta	LOTUS Database	35616633
Sorbus decora	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Strychnos spinosa	LOTUS Database	35616633
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Syzygium formosanum	KNApSAcK Database	22123792
Terminalia brasiliensis	Plant	KNApSAcK
Vladimiria muliensis	-	KNApSAcK
Vochysia ferruginea	LOTUS Database	35616633
Woodwardia radicans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

triterpenoid (CHEBI:67894 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	523.70 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.0002 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	9.130 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
Water Solubility	0.00027 g/L	ALOGPS
logP	6.13	ALOGPS
logP	6.11	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	18.95	ChemAxon
pKa (Strongest Basic)	-0.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.76 m³·mol⁻¹	ChemAxon
Polarizability	54.68 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0002391

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013518

KNApSAcK ID

C00032467

Chemspider ID

83774

KEGG Compound ID

Not Available

BioCyc ID

CPD-14494

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92802

PDB ID

Not Available

ChEBI ID

519375

Good Scents ID

rw1296251

References

General References

Marquez-Martin A, De La Puerta R, Fernandez-Arche A, Ruiz-Gutierrez V, Yaqoob P: Modulation of cytokine secretion by pentacyclic triterpenes from olive pomace oil in human mononuclear cells. Cytokine. 2006 Dec;36(5-6):211-7. Epub 2007 Feb 9. [PubMed:17292619 ]
Ghorai S, Bag BG: Garland, Flower, and Petals via a Hierarchical Self-Assembly of Ursane-Type Triterpenoid Uvaol. ACS Omega. 2021 Jul 27;6(31):20560-20568. doi: 10.1021/acsomega.1c02630. eCollection 2021 Aug 10. [PubMed:34396001 ]
Kazakova O, Tret'yakova E, Baev D: Evaluation of A-azepano-triterpenoids and related derivatives as antimicrobial and antiviral agents. J Antibiot (Tokyo). 2021 Jul 12. pii: 10.1038/s41429-021-00448-9. doi: 10.1038/s41429-021-00448-9. [PubMed:34253887 ]
Bano Z, Begum S, Ali SS, Kiran Z, Siddiqui BS, Ahmed A, Khawaja S, Fatima F, Jabeen A: Phytochemicals from Carissa carandas with potent cytotoxic and anti-inflammatory activities. Nat Prod Res. 2021 Feb 14:1-6. doi: 10.1080/14786419.2021.1886101. [PubMed:33583281 ]
Demirag O, Konuskan DB: Quality Properties, Fatty Acid and Sterol Compositions of East Mediterranean Region Olive Oils. J Oleo Sci. 2021;70(1):51-58. doi: 10.5650/jos.ess20179. [PubMed:33431772 ]
Carmo J, Cavalcante-Araujo P, Silva J, Ferro J, Correia AC, Lagente V, Barreto E: Uvaol Improves the Functioning of Fibroblasts and Endothelial Cells and Accelerates the Healing of Cutaneous Wounds in Mice. Molecules. 2020 Oct 28;25(21). pii: molecules25214982. doi: 10.3390/molecules25214982. [PubMed:33126422 ]
Sadeer NB, Mahomoodally MF: Antibiotic Potentiation of Natural Products: A Promising Target to Fight Pathogenic Bacteria. Curr Drug Targets. 2021;22(5):555-572. doi: 10.2174/1389450121666200924113740. [PubMed:32972338 ]
Bonel-Perez GC, Perez-Jimenez A, Gris-Cardenas I, Parra-Perez AM, Lupianez JA, Reyes-Zurita FJ, Siles E, Csuk R, Peragon J, Rufino-Palomares EE: Antiproliferative and Pro-Apoptotic Effect of Uvaol in Human Hepatocarcinoma HepG2 Cells by Affecting G0/G1 Cell Cycle Arrest, ROS Production and AKT/PI3K Signaling Pathway. Molecules. 2020 Sep 16;25(18). pii: molecules25184254. doi: 10.3390/molecules25184254. [PubMed:32947962 ]
Huang H, Lian Q, Wang L, Shan Y, Li F, Chang SK, Jiang Y: Chemical composition of the cuticular membrane in guava fruit (Psidium guajava L.) affects barrier property to transpiration. Plant Physiol Biochem. 2020 Oct;155:589-595. doi: 10.1016/j.plaphy.2020.08.023. Epub 2020 Aug 14. [PubMed:32846394 ]
Bakir D, Akdeniz M, Ertas A, Yilmaz MA, Yener I, Firat M, Kolak U: A GC-MS method validation for quantitative investigation of some chemical markers in Salvia hypargeia Fisch. & C.A. Mey. of Turkey: Enzyme inhibitory potential of ferruginol. J Food Biochem. 2020 Sep;44(9):e13350. doi: 10.1111/jfbc.13350. Epub 2020 Jul 19. [PubMed:32686189 ]
Du SY, Huang HF, Li XQ, Zhai LX, Zhu QC, Zheng K, Song X, Xu CS, Li CY, Li Y, He ZD, Xiao HT: Anti-inflammatory properties of uvaol on DSS-induced colitis and LPS-stimulated macrophages. Chin Med. 2020 May 7;15:43. doi: 10.1186/s13020-020-00322-0. eCollection 2020. [PubMed:32411289 ]
Wang W, Wang W, Ge H, Li G, Shen P, Xu S, Yu B, Zhang J: Biocatalytic allylic hydroxylation of unsaturated triterpenes and steroids by Bacillus megaterium CGMCC 1.1741. Bioorg Chem. 2020 Jun;99:103826. doi: 10.1016/j.bioorg.2020.103826. Epub 2020 Apr 6. [PubMed:32315895 ]

Showing NP-Card for Uvaol (NP0001372)

MOL for NP0001372 (Uvaol)

3D MOL for NP0001372 (Uvaol)

3D SDF for NP0001372 (Uvaol)

3D-SDF for NP0001372 (Uvaol)

PDB for NP0001372 (Uvaol)

3D PDB for NP0001372 (Uvaol)

SMILES for NP0001372 (Uvaol)

INCHI for NP0001372 (Uvaol)

Structure for NP0001372 (Uvaol)

3D Structure for NP0001372 (Uvaol)