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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:33:23 UTC

Update Date

2022-11-23 22:29:21 UTC

HMDB ID

HMDB0259730

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Usnic Acid

Description

4,10-diacetyl-11,13-dihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraene-3,5-dione belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure. Based on a literature review very few articles have been published on 4,10-diacetyl-11,13-dihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),6,9,11-tetraene-3,5-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). Usnic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Usnic Acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0259730
     RDKit          3D
usnic acid
 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.8662    1.4227   -1.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4331    1.1221   -1.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9301    1.3464   -2.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5525    0.5665   -0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0508    0.2971    0.7711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3759    0.5591    1.0586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2231   -0.2266    1.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7380   -0.5206    3.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8977   -0.4847    1.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1172   -1.0096    2.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3585   -0.2409    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2258    0.2967   -0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5314    0.5053   -1.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605    0.1458   -1.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8322    0.2024   -2.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191   -0.3213   -2.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9624   -0.8969   -2.7932 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028   -0.1408   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3903    0.9586   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185    1.3106    0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8424    1.5613   -1.4242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    0.1561    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1036    0.8650    1.0317 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9148   -0.4610   -0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241   -1.9527   -0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3006    1.8880   -2.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9960    2.1853   -0.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4587    0.5301   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8038    0.3945    1.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5307   -1.3006    3.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2523    0.3964    3.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413   -0.7953    3.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8486   -1.2193    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841    0.6104   -3.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8204   -1.1243   -0.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1842    2.0919    1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8833    1.6769    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202    0.3680    1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184   -2.2043   -1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8791   -2.2167    0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2524   -2.4834   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 18 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 12  4  1  0
 24 14  1  0
 24 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 15 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 25 39  1  0
 25 40  1  0
 25 41  1  0
M  END


  Mrv0541 02241204472D          

 25 27  0  0  0  0            999 V2000
   -3.0091   -0.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021    0.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9471    0.7913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6501   -0.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9050   -1.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7120   -1.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3530   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5460   -1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215   -2.3175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7889   -1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5340   -1.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0860   -0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8310    0.3498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8930   -0.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4450    0.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1479   -1.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549   -1.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5959   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8508   -2.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2988   -3.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6578   -2.9602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910   -1.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445   -0.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8431   -0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5881    0.3498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 11 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259730

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)C1C(=O)C=C2OC3=C(C(O)=C(C)C(O)=C3C(C)=O)C2(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3

> <INCHI_KEY>
CUCUKLJLRRAKFN-UHFFFAOYSA-N

> <FORMULA>
C18H16O7

> <MOLECULAR_WEIGHT>
344.3154

> <EXACT_MASS>
344.089602866

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
33.93241028171306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,10-diacetyl-11,13-dihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraene-3,5-dione

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
2.389541400333333

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.559624399189648

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.644266152190405

> <JCHEM_PKA_STRONGEST_BASIC>
-4.044774996074257

> <JCHEM_POLAR_SURFACE_AREA>
117.97

> <JCHEM_REFRACTIVITY>
88.54719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-(S)-usnate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259730
     RDKit          3D
usnic acid
 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.8662    1.4227   -1.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4331    1.1221   -1.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9301    1.3464   -2.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5525    0.5665   -0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0508    0.2971    0.7711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3759    0.5591    1.0586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2231   -0.2266    1.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7380   -0.5206    3.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8977   -0.4847    1.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1172   -1.0096    2.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3585   -0.2409    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2258    0.2967   -0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5314    0.5053   -1.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605    0.1458   -1.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8322    0.2024   -2.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191   -0.3213   -2.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9624   -0.8969   -2.7932 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028   -0.1408   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3903    0.9586   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185    1.3106    0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8424    1.5613   -1.4242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    0.1561    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1036    0.8650    1.0317 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9148   -0.4610   -0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241   -1.9527   -0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3006    1.8880   -2.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9960    2.1853   -0.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4587    0.5301   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8038    0.3945    1.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5307   -1.3006    3.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2523    0.3964    3.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413   -0.7953    3.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8486   -1.2193    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841    0.6104   -3.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8204   -1.1243   -0.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1842    2.0919    1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8833    1.6769    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202    0.3680    1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184   -2.2043   -1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8791   -2.2167    0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2524   -2.4834   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 18 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 12  4  1  0
 24 14  1  0
 24 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 15 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 25 39  1  0
 25 40  1  0
 25 41  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.617  -0.308   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.111   0.013   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.635   1.477   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.080  -1.132   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.556  -2.597   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.062  -2.917   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.526  -3.741   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.019  -3.421   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.227  -4.326   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.473  -3.421   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.997  -1.956   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.027  -0.812   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.551   0.653   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.534  -1.132   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.564   0.013   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.009  -2.597   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.516  -2.917   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.979  -3.741   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.455  -5.206   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.424  -6.350   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.961  -5.526   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.543  -1.956   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.083  -0.549   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.574  -0.812   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.098   0.653   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   24                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   10   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   11    8   23   24                                             
CONECT   23   22                                                            
CONECT   24   22    4   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0259730
HETATM    1  C1  UNL     1      -4.866   1.423  -1.270  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.433   1.122  -1.526  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.930   1.346  -2.663  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.553   0.566  -0.505  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.051   0.297   0.771  1.00  0.00           C  
HETATM    6  O2  UNL     1      -4.376   0.559   1.059  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.223  -0.227   1.735  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.738  -0.521   3.110  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.898  -0.485   1.428  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.117  -1.010   2.431  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.359  -0.241   0.193  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.226   0.297  -0.769  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.531   0.505  -1.967  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.760   0.146  -1.853  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.832   0.202  -2.617  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.119  -0.321  -2.086  1.00  0.00           C  
HETATM   17  O5  UNL     1       3.962  -0.897  -2.793  1.00  0.00           O  
HETATM   18  C13 UNL     1       3.403  -0.141  -0.628  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.390   0.959  -0.459  1.00  0.00           C  
HETATM   20  C15 UNL     1       4.819   1.311   0.922  1.00  0.00           C  
HETATM   21  O6  UNL     1       4.842   1.561  -1.424  1.00  0.00           O  
HETATM   22  C16 UNL     1       2.122   0.156   0.073  1.00  0.00           C  
HETATM   23  O7  UNL     1       2.104   0.865   1.032  1.00  0.00           O  
HETATM   24  C17 UNL     1       0.915  -0.461  -0.474  1.00  0.00           C  
HETATM   25  C18 UNL     1       1.224  -1.953  -0.627  1.00  0.00           C  
HETATM   26  H1  UNL     1      -5.301   1.888  -2.206  1.00  0.00           H  
HETATM   27  H2  UNL     1      -4.996   2.185  -0.476  1.00  0.00           H  
HETATM   28  H3  UNL     1      -5.459   0.530  -0.994  1.00  0.00           H  
HETATM   29  H4  UNL     1      -4.804   0.395   1.942  1.00  0.00           H  
HETATM   30  H5  UNL     1      -3.531  -1.301   3.041  1.00  0.00           H  
HETATM   31  H6  UNL     1      -3.252   0.396   3.470  1.00  0.00           H  
HETATM   32  H7  UNL     1      -1.941  -0.795   3.800  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.849  -1.219   2.249  1.00  0.00           H  
HETATM   34  H9  UNL     1       1.784   0.610  -3.597  1.00  0.00           H  
HETATM   35  H10 UNL     1       3.820  -1.124  -0.288  1.00  0.00           H  
HETATM   36  H11 UNL     1       4.184   2.092   1.382  1.00  0.00           H  
HETATM   37  H12 UNL     1       5.883   1.677   0.877  1.00  0.00           H  
HETATM   38  H13 UNL     1       4.820   0.368   1.510  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.618  -2.204  -1.614  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.879  -2.217   0.227  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.252  -2.483  -0.412  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    3    4
CONECT    4    5    5   12
CONECT    5    6    7
CONECT    6   29
CONECT    7    8    9    9
CONECT    8   30   31   32
CONECT    9   10   11
CONECT   10   33
CONECT   11   12   12   24
CONECT   12   13
CONECT   13   14
CONECT   14   15   15   24
CONECT   15   16   34
CONECT   16   17   17   18
CONECT   18   19   22   35
CONECT   19   20   21   21
CONECT   20   36   37   38
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   39   40   41
END

HMDB0259730
     RDKit          3D
usnic acid
 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.8662    1.4227   -1.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4331    1.1221   -1.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9301    1.3464   -2.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5525    0.5665   -0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0508    0.2971    0.7711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3759    0.5591    1.0586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2231   -0.2266    1.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7380   -0.5206    3.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8977   -0.4847    1.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1172   -1.0096    2.4308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3585   -0.2409    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2258    0.2967   -0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5314    0.5053   -1.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605    0.1458   -1.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8322    0.2024   -2.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191   -0.3213   -2.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9624   -0.8969   -2.7932 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028   -0.1408   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3903    0.9586   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185    1.3106    0.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8424    1.5613   -1.4242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1225    0.1561    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1036    0.8650    1.0317 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9148   -0.4610   -0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241   -1.9527   -0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3006    1.8880   -2.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9960    2.1853   -0.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4587    0.5301   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8038    0.3945    1.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5307   -1.3006    3.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2523    0.3964    3.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413   -0.7953    3.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8486   -1.2193    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841    0.6104   -3.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8204   -1.1243   -0.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1842    2.0919    1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8833    1.6769    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202    0.3680    1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184   -2.2043   -1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8791   -2.2167    0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2524   -2.4834   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 18 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 12  4  1  0
 24 14  1  0
 24 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 15 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 25 39  1  0
 25 40  1  0
 25 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9BH)-dibenzofurandione	MeSH
Usnate	Generator

Chemical Formula

C₁₈H₁₆O₇

Average Molecular Weight

344.3154

Monoisotopic Molecular Weight

344.089602866

IUPAC Name

4,10-diacetyl-11,13-dihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraene-3,5-dione

Traditional Name

7-hydroxy-(S)-usnate

CAS Registry Number

Not Available

SMILES

CC(=O)C1C(=O)C=C2OC3=C(C(O)=C(C)C(O)=C3C(C)=O)C2(C)C1=O

InChI Identifier

InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3

InChI Key

CUCUKLJLRRAKFN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Acetophenones

Direct Parent

Acetophenones

Alternative Parents

Substituents

Acetophenone
Coumaran
Aryl ketone
Aryl alkyl ketone
Cyclohexenone
1,3-diketone
1,3-dicarbonyl compound
Vinylogous ester
Vinylogous acid
Ketone
Cyclic ketone
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzofurans (CHEBI:2264 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

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
logP	2.77	ALOGPS
logP	2.39	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	117.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.55 m³·mol⁻¹	ChemAxon
Polarizability	33.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	176.892	32859911
AllCCS	[M+H-H2O]+	173.83	32859911
AllCCS	[M+Na]+	180.536	32859911
AllCCS	[M+NH4]+	179.724	32859911
AllCCS	[M-H]-	183.242	32859911
AllCCS	[M+Na-2H]-	183.082	32859911
AllCCS	[M+HCOO]-	183.046	32859911
DeepCCS	[M+H]+	184.355	30932474
DeepCCS	[M-H]-	181.997	30932474
DeepCCS	[M-2H]-	216.15	30932474
DeepCCS	[M+Na]+	191.378	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
usnic acid	CC(=O)C1C(=O)C=C2OC3=C(C(O)=C(C)C(O)=C3C(C)=O)C2(C)C1=O	4139.0	Standard polar	33892256
usnic acid	CC(=O)C1C(=O)C=C2OC3=C(C(O)=C(C)C(O)=C3C(C)=O)C2(C)C1=O	2405.8	Standard non polar	33892256
usnic acid	CC(=O)C1C(=O)C=C2OC3=C(C(O)=C(C)C(O)=C3C(C)=O)C2(C)C1=O	2714.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
usnic acid,3TMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C3C2(C)C1=O	2800.6	Semi standard non polar	33892256
usnic acid,3TMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C3C2(C)C1=O	2824.1	Standard non polar	33892256
usnic acid,3TMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C3C2(C)C1=O	3108.7	Standard polar	33892256
usnic acid,3TMS,isomer #2	CC(=O)C1=C(O[Si](C)(C)C)C(C)=C(O[Si](C)(C)C)C2=C1OC1=CC(=O)C(=C(C)O[Si](C)(C)C)C(=O)C12C	2844.6	Semi standard non polar	33892256
usnic acid,3TMS,isomer #2	CC(=O)C1=C(O[Si](C)(C)C)C(C)=C(O[Si](C)(C)C)C2=C1OC1=CC(=O)C(=C(C)O[Si](C)(C)C)C(=O)C12C	2871.6	Standard non polar	33892256
usnic acid,3TMS,isomer #2	CC(=O)C1=C(O[Si](C)(C)C)C(C)=C(O[Si](C)(C)C)C2=C1OC1=CC(=O)C(=C(C)O[Si](C)(C)C)C(=O)C12C	3135.7	Standard polar	33892256
usnic acid,3TMS,isomer #3	CC(=O)C1=C(O[Si](C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C12	2766.5	Semi standard non polar	33892256
usnic acid,3TMS,isomer #3	CC(=O)C1=C(O[Si](C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C12	2843.8	Standard non polar	33892256
usnic acid,3TMS,isomer #3	CC(=O)C1=C(O[Si](C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C12	3150.2	Standard polar	33892256
usnic acid,3TMS,isomer #4	C=C(O[Si](C)(C)C)C1C(=O)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C3C2(C)C1=O	2811.4	Semi standard non polar	33892256
usnic acid,3TMS,isomer #4	C=C(O[Si](C)(C)C)C1C(=O)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C3C2(C)C1=O	2858.9	Standard non polar	33892256
usnic acid,3TMS,isomer #4	C=C(O[Si](C)(C)C)C1C(=O)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C3C2(C)C1=O	3122.8	Standard polar	33892256
usnic acid,3TMS,isomer #5	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2OC3=C(C(C)=O)C(O)=C(C)C(O[Si](C)(C)C)=C3C2(C)C1=O	2769.0	Semi standard non polar	33892256
usnic acid,3TMS,isomer #5	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2OC3=C(C(C)=O)C(O)=C(C)C(O[Si](C)(C)C)=C3C2(C)C1=O	2895.2	Standard non polar	33892256
usnic acid,3TMS,isomer #5	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2OC3=C(C(C)=O)C(O)=C(C)C(O[Si](C)(C)C)=C3C2(C)C1=O	3290.5	Standard polar	33892256
usnic acid,3TMS,isomer #6	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O)=C(C)C(O[Si](C)(C)C)=C12	2754.9	Semi standard non polar	33892256
usnic acid,3TMS,isomer #6	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O)=C(C)C(O[Si](C)(C)C)=C12	2901.5	Standard non polar	33892256
usnic acid,3TMS,isomer #6	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O)=C(C)C(O[Si](C)(C)C)=C12	3328.8	Standard polar	33892256
usnic acid,3TMS,isomer #7	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O)=C3C2(C)C1=O	2746.4	Semi standard non polar	33892256
usnic acid,3TMS,isomer #7	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O)=C3C2(C)C1=O	2920.7	Standard non polar	33892256
usnic acid,3TMS,isomer #7	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O)=C3C2(C)C1=O	3346.5	Standard polar	33892256
usnic acid,3TMS,isomer #8	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O)=C12	2743.0	Semi standard non polar	33892256
usnic acid,3TMS,isomer #8	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O)=C12	2920.3	Standard non polar	33892256
usnic acid,3TMS,isomer #8	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O)=C12	3339.8	Standard polar	33892256
usnic acid,4TMS,isomer #1	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C3C2(C)C1=O	2821.2	Semi standard non polar	33892256
usnic acid,4TMS,isomer #1	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C3C2(C)C1=O	2910.5	Standard non polar	33892256
usnic acid,4TMS,isomer #1	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C3C2(C)C1=O	3066.4	Standard polar	33892256
usnic acid,4TMS,isomer #2	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C12	2802.5	Semi standard non polar	33892256
usnic acid,4TMS,isomer #2	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C12	2935.6	Standard non polar	33892256
usnic acid,4TMS,isomer #2	C=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)=C12	3097.5	Standard polar	33892256
usnic acid,3TBDMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2(C)C1=O	3461.6	Semi standard non polar	33892256
usnic acid,3TBDMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2(C)C1=O	3442.8	Standard non polar	33892256
usnic acid,3TBDMS,isomer #1	CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2(C)C1=O	3425.3	Standard polar	33892256
usnic acid,3TBDMS,isomer #2	CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(C)=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=CC(=O)C(=C(C)O[Si](C)(C)C(C)(C)C)C(=O)C12C	3540.9	Semi standard non polar	33892256
usnic acid,3TBDMS,isomer #2	CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(C)=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=CC(=O)C(=C(C)O[Si](C)(C)C(C)(C)C)C(=O)C12C	3494.7	Standard non polar	33892256
usnic acid,3TBDMS,isomer #2	CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(C)=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=CC(=O)C(=C(C)O[Si](C)(C)C(C)(C)C)C(=O)C12C	3451.7	Standard polar	33892256
usnic acid,3TBDMS,isomer #3	CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C12	3459.8	Semi standard non polar	33892256
usnic acid,3TBDMS,isomer #3	CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C12	3450.5	Standard non polar	33892256
usnic acid,3TBDMS,isomer #3	CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C12	3460.6	Standard polar	33892256
usnic acid,3TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)C1C(=O)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2(C)C1=O	3473.1	Semi standard non polar	33892256
usnic acid,3TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)C1C(=O)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2(C)C1=O	3466.1	Standard non polar	33892256
usnic acid,3TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)C1C(=O)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2(C)C1=O	3426.1	Standard polar	33892256
usnic acid,3TBDMS,isomer #5	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(C(C)=O)C(O)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2(C)C1=O	3432.3	Semi standard non polar	33892256
usnic acid,3TBDMS,isomer #5	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(C(C)=O)C(O)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2(C)C1=O	3491.2	Standard non polar	33892256
usnic acid,3TBDMS,isomer #5	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(C(C)=O)C(O)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2(C)C1=O	3535.3	Standard polar	33892256
usnic acid,3TBDMS,isomer #6	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O)=C(C)C(O[Si](C)(C)C(C)(C)C)=C12	3440.4	Semi standard non polar	33892256
usnic acid,3TBDMS,isomer #6	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O)=C(C)C(O[Si](C)(C)C(C)(C)C)=C12	3496.7	Standard non polar	33892256
usnic acid,3TBDMS,isomer #6	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O)=C(C)C(O[Si](C)(C)C(C)(C)C)=C12	3563.9	Standard polar	33892256
usnic acid,3TBDMS,isomer #7	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O)=C3C2(C)C1=O	3402.4	Semi standard non polar	33892256
usnic acid,3TBDMS,isomer #7	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O)=C3C2(C)C1=O	3514.4	Standard non polar	33892256
usnic acid,3TBDMS,isomer #7	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O)=C3C2(C)C1=O	3601.4	Standard polar	33892256
usnic acid,3TBDMS,isomer #8	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O)=C12	3415.9	Semi standard non polar	33892256
usnic acid,3TBDMS,isomer #8	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O)=C12	3517.8	Standard non polar	33892256
usnic acid,3TBDMS,isomer #8	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O)=C12	3592.8	Standard polar	33892256
usnic acid,4TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2(C)C1=O	3648.4	Semi standard non polar	33892256
usnic acid,4TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2(C)C1=O	3640.5	Standard non polar	33892256
usnic acid,4TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C3C2(C)C1=O	3440.5	Standard polar	33892256
usnic acid,4TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C12	3658.6	Semi standard non polar	33892256
usnic acid,4TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C12	3660.0	Standard non polar	33892256
usnic acid,4TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C2(C)C(=CC1=O)OC1=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)=C12	3461.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-6289000000-24f885e6ce84efc8666e	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Usnic Acid GC-MS (TBDMS_1_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Usnic Acid 10V, Negative-QTOF	splash10-0006-0009000000-8529f7e2fc24cc2d2eea	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Usnic Acid 40V, Negative-QTOF	splash10-03gi-0394000000-23a711c12ce3792a5098	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Usnic Acid 20V, Negative-QTOF	splash10-056r-0079000000-910689424749b20916c9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Usnic Acid 10V, Positive-QTOF	splash10-002b-0009000000-86385e1c88063c7f9e6c	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Usnic Acid 20V, Positive-QTOF	splash10-004j-0109000000-e88990b8900522f06abf	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Usnic Acid 40V, Positive-QTOF	splash10-0btl-6695000000-c2833b897d51d2cbd56d	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Usnic Acid 10V, Negative-QTOF	splash10-0006-0009000000-4cbcc44f66d8ec7fa68b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Usnic Acid 20V, Negative-QTOF	splash10-0udi-0059000000-35648b46b5fadeabfa24	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Usnic Acid 40V, Negative-QTOF	splash10-02di-3951000000-fe24f4d5b98ed6ab4370	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5444

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Usnic Acid (HMDB0259730)

MOL for HMDB0259730 (Usnic Acid)

3D MOL for HMDB0259730 (Usnic Acid)

3D SDF for HMDB0259730 (Usnic Acid)

3D-SDF for HMDB0259730 (Usnic Acid)

PDB for HMDB0259730 (Usnic Acid)

3D PDB for HMDB0259730 (Usnic Acid)

SMILES for HMDB0259730 (Usnic Acid)

INCHI for HMDB0259730 (Usnic Acid)

Structure for HMDB0259730 (Usnic Acid)

3D Structure for HMDB0259730 (Usnic Acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra