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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:13:25 UTC

Update Date

2022-03-07 02:55:08 UTC

HMDB ID

HMDB0036981

Secondary Accession Numbers

HMDB36981

Metabolite Identification

Common Name

Atrovirinone

Description

Atrovirinone belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6). Based on a literature review a significant number of articles have been published on Atrovirinone.

Structure

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

  Mrv0541 02241219042D          

 33 34  0  0  0  0            999 V2000
   -3.2127    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2127   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4983   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4983    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700    0.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7869   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7869    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9269   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9269    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4983    1.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2141    1.8572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7828    1.8572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9269    0.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4983   -1.8572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700   -1.0314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700   -1.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599    1.4443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141    1.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141   -1.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599   -1.8572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0686    1.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 26  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
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 27  1  0  0  0  0
 10 11  1  0  0  0  0
 10 32  2  0  0  0  0
 11 12  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 29  2  0  0  0  0
 14 15  1  0  0  0  0
 15 18  2  0  0  0  0
 16 17  1  0  0  0  0
 16 21  2  0  0  0  0
 18 19  1  0  0  0  0
 18 31  1  0  0  0  0
 20 21  1  0  0  0  0
 21 30  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 33  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0036981
     RDKit          3D
Atrovirinone
 61 62  0  0  0  0  0  0  0  0999 V2000
    6.2337   -0.0206    3.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0715   -0.0941    2.2056 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8747   -0.0534    1.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8516    0.0581    2.2973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6862   -0.1275    0.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7301   -0.2497   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0478   -0.3132   -0.3773 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -0.3195   -2.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2456   -0.2627   -2.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0554   -0.3334   -4.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008   -0.1410   -1.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -0.0728   -0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485    0.0504    0.5107 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0233    0.1150    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5316    1.2942   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302    2.4268   -0.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4947    3.1828   -1.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8647    1.3290   -0.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3320    2.4460   -0.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6872    0.0941   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0878    0.2506   -1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8174    1.2069   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4228    2.2744   -0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4337    2.6098   -2.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1330    3.1933    0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1963   -1.0795   -0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9563   -2.3461   -0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932   -2.9447    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1699   -3.1361    1.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4541   -2.7863    1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095   -3.7319    3.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315   -1.0949    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130   -2.2267    0.4360 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276   -0.1438    3.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9469    0.9794    3.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7105   -0.8398    4.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3711   -0.2798    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3836   -0.4149   -2.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0481    0.5327   -4.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808   -0.0959   -2.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459    3.5588   -1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9049    2.4775   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2666    3.9650   -1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6990   -0.6306   -1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    0.7500   -2.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8419    1.0057    0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7020    1.7070   -2.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3099    3.3006   -2.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5129    3.0881   -2.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4801    2.6588    1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0106    3.6413   -0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4075    4.0018    0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9343   -2.3432   -0.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3683   -3.1260   -0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0822   -3.2076    1.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3250   -3.1672    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5602   -1.6934    0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819   -3.2692    0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3738   -2.9562    3.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533   -4.4698    3.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2382   -4.2265    3.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  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  1  0
 15 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 23 25  1  0
 20 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  3
 29 30  1  0
 29 31  1  0
 26 32  1  0
 32 33  2  0
 12  5  1  0
 32 14  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  7 37  1  0
  8 38  1  0
 10 39  1  0
 11 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 24 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 30 56  1  0
 30 57  1  0
 30 58  1  0
 31 59  1  0
 31 60  1  0
 31 61  1  0
M  END

  Mrv0541 02241219042D          

 33 34  0  0  0  0            999 V2000
   -3.2127    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2127   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4983   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4983    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700    0.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7869   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7869    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9269   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9269    0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4983    1.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2141    1.8572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7828    1.8572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9269    0.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4983   -1.8572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700   -1.0314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700   -1.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599    1.4443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141    1.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141   -1.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599   -1.8572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0686    1.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 26  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
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 27  1  0  0  0  0
 10 11  1  0  0  0  0
 10 32  2  0  0  0  0
 11 12  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 29  2  0  0  0  0
 14 15  1  0  0  0  0
 15 18  2  0  0  0  0
 16 17  1  0  0  0  0
 16 21  2  0  0  0  0
 18 19  1  0  0  0  0
 18 31  1  0  0  0  0
 20 21  1  0  0  0  0
 21 30  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 33  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036981

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1=C(OC2=C(OC)C(=O)C(CC=C(C)C)=C(CC=C(C)C)C2=O)C=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O8/c1-13(2)7-9-16-17(10-8-14(3)4)22(29)24(23(31-5)21(16)28)33-19-12-15(26)11-18(27)20(19)25(30)32-6/h7-8,11-12,26-27H,9-10H2,1-6H3

> <INCHI_KEY>
AATISISCRVORPT-UHFFFAOYSA-N

> <FORMULA>
C25H28O8

> <MOLECULAR_WEIGHT>
456.485

> <EXACT_MASS>
456.178417872

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
47.8874696618758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2,4-dihydroxy-6-{[2-methoxy-4,5-bis(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl]oxy}benzoate

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
5.171216862

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.997408876073463

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.14714764552412

> <JCHEM_PKA_STRONGEST_BASIC>
-4.160685433745578

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
127.07919999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.14e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2,4-dihydroxy-6-{[2-methoxy-4,5-bis(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl]oxy}benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036981
     RDKit          3D
Atrovirinone
 61 62  0  0  0  0  0  0  0  0999 V2000
    6.2337   -0.0206    3.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0715   -0.0941    2.2056 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8747   -0.0534    1.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8516    0.0581    2.2973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6862   -0.1275    0.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7301   -0.2497   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0478   -0.3132   -0.3773 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -0.3195   -2.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2456   -0.2627   -2.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0554   -0.3334   -4.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008   -0.1410   -1.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -0.0728   -0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485    0.0504    0.5107 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0233    0.1150    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5316    1.2942   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302    2.4268   -0.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4947    3.1828   -1.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8647    1.3290   -0.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3320    2.4460   -0.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6872    0.0941   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0878    0.2506   -1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8174    1.2069   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4228    2.2744   -0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4337    2.6098   -2.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1330    3.1933    0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1963   -1.0795   -0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9563   -2.3461   -0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932   -2.9447    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1699   -3.1361    1.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4541   -2.7863    1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095   -3.7319    3.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315   -1.0949    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130   -2.2267    0.4360 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276   -0.1438    3.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9469    0.9794    3.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7105   -0.8398    4.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3711   -0.2798    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3836   -0.4149   -2.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0481    0.5327   -4.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808   -0.0959   -2.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459    3.5588   -1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9049    2.4775   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2666    3.9650   -1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6990   -0.6306   -1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    0.7500   -2.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8419    1.0057    0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7020    1.7070   -2.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3099    3.3006   -2.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5129    3.0881   -2.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4801    2.6588    1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0106    3.6413   -0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4075    4.0018    0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9343   -2.3432   -0.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3683   -3.1260   -0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0822   -3.2076    1.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3250   -3.1672    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5602   -1.6934    0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819   -3.2692    0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3738   -2.9562    3.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533   -4.4698    3.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2382   -4.2265    3.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  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  1  0
 15 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 23 25  1  0
 20 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  3
 29 30  1  0
 29 31  1  0
 26 32  1  0
 32 33  2  0
 12  5  1  0
 32 14  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  7 37  1  0
  8 38  1  0
 10 39  1  0
 11 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 24 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 30 56  1  0
 30 57  1  0
 30 58  1  0
 31 59  1  0
 31 60  1  0
 31 61  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      -5.997   0.387   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.997  -1.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.664  -1.925   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.333  -1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.333   0.387   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.664   1.155   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.997   1.157   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.662   0.387   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.662  -1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.672  -1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.002  -1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.002   0.387   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.672   1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.336  -1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.666  -1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.666   0.387   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.336   1.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.000  -1.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.330  -1.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.330   0.387   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.000   1.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.664   2.696   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.000   3.467   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -3.328   3.467   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -7.330   1.157   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -4.664  -3.467   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.997  -1.925   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.997  -3.467   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.672   2.696   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.000   2.696   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.000  -3.467   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.672  -3.467   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.995   2.696   0.000  0.00  0.00           C+0
CONECT    1    2    6   25                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    1    5   22                                                  
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   27                                                  
CONECT   10    9   11   32                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13   17                                                  
CONECT   13    8   12   29                                                  
CONECT   14   11   15                                                       
CONECT   15   14   18                                                       
CONECT   16   17   21                                                       
CONECT   17   12   16                                                       
CONECT   18   15   19   31                                                  
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21   16   20   30                                                  
CONECT   22    6   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   33                                                       
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    9   28                                                       
CONECT   28   27                                                            
CONECT   29   13                                                            
CONECT   30   21                                                            
CONECT   31   18                                                            
CONECT   32   10                                                            
CONECT   33   24                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

COMPND    HMDB0036981
HETATM    1  C1  UNL     1       6.234  -0.021   3.614  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.072  -0.094   2.206  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.875  -0.053   1.564  1.00  0.00           C  
HETATM    4  O2  UNL     1       3.852   0.058   2.297  1.00  0.00           O  
HETATM    5  C3  UNL     1       4.686  -0.127   0.118  1.00  0.00           C  
HETATM    6  C4  UNL     1       5.730  -0.250  -0.771  1.00  0.00           C  
HETATM    7  O3  UNL     1       7.048  -0.313  -0.377  1.00  0.00           O  
HETATM    8  C5  UNL     1       5.529  -0.320  -2.160  1.00  0.00           C  
HETATM    9  C6  UNL     1       4.246  -0.263  -2.628  1.00  0.00           C  
HETATM   10  O4  UNL     1       4.055  -0.333  -4.019  1.00  0.00           O  
HETATM   11  C7  UNL     1       3.201  -0.141  -1.748  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.388  -0.073  -0.401  1.00  0.00           C  
HETATM   13  O5  UNL     1       2.348   0.050   0.511  1.00  0.00           O  
HETATM   14  C9  UNL     1       1.023   0.115   0.127  1.00  0.00           C  
HETATM   15  C10 UNL     1       0.532   1.294  -0.211  1.00  0.00           C  
HETATM   16  O6  UNL     1       1.330   2.427  -0.178  1.00  0.00           O  
HETATM   17  C11 UNL     1       1.495   3.183  -1.387  1.00  0.00           C  
HETATM   18  C12 UNL     1      -0.865   1.329  -0.610  1.00  0.00           C  
HETATM   19  O7  UNL     1      -1.332   2.446  -0.930  1.00  0.00           O  
HETATM   20  C13 UNL     1      -1.687   0.094  -0.632  1.00  0.00           C  
HETATM   21  C14 UNL     1      -3.088   0.251  -1.048  1.00  0.00           C  
HETATM   22  C15 UNL     1      -3.817   1.207  -0.144  1.00  0.00           C  
HETATM   23  C16 UNL     1      -4.423   2.274  -0.629  1.00  0.00           C  
HETATM   24  C17 UNL     1      -4.434   2.610  -2.076  1.00  0.00           C  
HETATM   25  C18 UNL     1      -5.133   3.193   0.328  1.00  0.00           C  
HETATM   26  C19 UNL     1      -1.196  -1.079  -0.295  1.00  0.00           C  
HETATM   27  C20 UNL     1      -1.956  -2.346  -0.295  1.00  0.00           C  
HETATM   28  C21 UNL     1      -1.993  -2.945   1.092  1.00  0.00           C  
HETATM   29  C22 UNL     1      -3.170  -3.136   1.666  1.00  0.00           C  
HETATM   30  C23 UNL     1      -4.454  -2.786   1.001  1.00  0.00           C  
HETATM   31  C24 UNL     1      -3.210  -3.732   3.048  1.00  0.00           C  
HETATM   32  C25 UNL     1       0.231  -1.095   0.109  1.00  0.00           C  
HETATM   33  O8  UNL     1       0.713  -2.227   0.436  1.00  0.00           O  
HETATM   34  H1  UNL     1       7.328  -0.144   3.801  1.00  0.00           H  
HETATM   35  H2  UNL     1       5.947   0.979   3.987  1.00  0.00           H  
HETATM   36  H3  UNL     1       5.711  -0.840   4.136  1.00  0.00           H  
HETATM   37  H4  UNL     1       7.371  -0.280   0.536  1.00  0.00           H  
HETATM   38  H5  UNL     1       6.384  -0.415  -2.810  1.00  0.00           H  
HETATM   39  H6  UNL     1       4.048   0.533  -4.556  1.00  0.00           H  
HETATM   40  H7  UNL     1       2.181  -0.096  -2.119  1.00  0.00           H  
HETATM   41  H8  UNL     1       0.546   3.559  -1.768  1.00  0.00           H  
HETATM   42  H9  UNL     1       1.905   2.477  -2.148  1.00  0.00           H  
HETATM   43  H10 UNL     1       2.267   3.965  -1.240  1.00  0.00           H  
HETATM   44  H11 UNL     1      -3.699  -0.631  -1.116  1.00  0.00           H  
HETATM   45  H12 UNL     1      -3.035   0.750  -2.067  1.00  0.00           H  
HETATM   46  H13 UNL     1      -3.842   1.006   0.938  1.00  0.00           H  
HETATM   47  H14 UNL     1      -4.702   1.707  -2.701  1.00  0.00           H  
HETATM   48  H15 UNL     1      -5.310   3.301  -2.264  1.00  0.00           H  
HETATM   49  H16 UNL     1      -3.513   3.088  -2.424  1.00  0.00           H  
HETATM   50  H17 UNL     1      -5.480   2.659   1.228  1.00  0.00           H  
HETATM   51  H18 UNL     1      -6.011   3.641  -0.181  1.00  0.00           H  
HETATM   52  H19 UNL     1      -4.407   4.002   0.556  1.00  0.00           H  
HETATM   53  H20 UNL     1      -2.934  -2.343  -0.732  1.00  0.00           H  
HETATM   54  H21 UNL     1      -1.368  -3.126  -0.881  1.00  0.00           H  
HETATM   55  H22 UNL     1      -1.082  -3.208   1.598  1.00  0.00           H  
HETATM   56  H23 UNL     1      -5.325  -3.167   1.610  1.00  0.00           H  
HETATM   57  H24 UNL     1      -4.560  -1.693   0.848  1.00  0.00           H  
HETATM   58  H25 UNL     1      -4.582  -3.269   0.014  1.00  0.00           H  
HETATM   59  H26 UNL     1      -3.374  -2.956   3.821  1.00  0.00           H  
HETATM   60  H27 UNL     1      -4.053  -4.470   3.103  1.00  0.00           H  
HETATM   61  H28 UNL     1      -2.238  -4.227   3.254  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   12
CONECT    6    7    8
CONECT    7   37
CONECT    8    9    9   38
CONECT    9   10   11
CONECT   10   39
CONECT   11   12   12   40
CONECT   12   13
CONECT   13   14
CONECT   14   15   15   32
CONECT   15   16   18
CONECT   16   17
CONECT   17   41   42   43
CONECT   18   19   19   20
CONECT   20   21   26   26
CONECT   21   22   44   45
CONECT   22   23   23   46
CONECT   23   24   25
CONECT   24   47   48   49
CONECT   25   50   51   52
CONECT   26   27   32
CONECT   27   28   53   54
CONECT   28   29   29   55
CONECT   29   30   31
CONECT   30   56   57   58
CONECT   31   59   60   61
CONECT   32   33   33
END

HMDB0036981
     RDKit          3D
Atrovirinone
 61 62  0  0  0  0  0  0  0  0999 V2000
    6.2337   -0.0206    3.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0715   -0.0941    2.2056 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8747   -0.0534    1.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8516    0.0581    2.2973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6862   -0.1275    0.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7301   -0.2497   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0478   -0.3132   -0.3773 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -0.3195   -2.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2456   -0.2627   -2.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0554   -0.3334   -4.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008   -0.1410   -1.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -0.0728   -0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485    0.0504    0.5107 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0233    0.1150    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5316    1.2942   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302    2.4268   -0.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4947    3.1828   -1.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8647    1.3290   -0.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3320    2.4460   -0.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6872    0.0941   -0.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0878    0.2506   -1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8174    1.2069   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4228    2.2744   -0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4337    2.6098   -2.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1330    3.1933    0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1963   -1.0795   -0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9563   -2.3461   -0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932   -2.9447    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1699   -3.1361    1.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4541   -2.7863    1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095   -3.7319    3.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315   -1.0949    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130   -2.2267    0.4360 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276   -0.1438    3.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9469    0.9794    3.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7105   -0.8398    4.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3711   -0.2798    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3836   -0.4149   -2.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0481    0.5327   -4.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808   -0.0959   -2.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459    3.5588   -1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9049    2.4775   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2666    3.9650   -1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6990   -0.6306   -1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    0.7500   -2.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8419    1.0057    0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7020    1.7070   -2.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3099    3.3006   -2.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5129    3.0881   -2.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4801    2.6588    1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0106    3.6413   -0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4075    4.0018    0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9343   -2.3432   -0.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3683   -3.1260   -0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0822   -3.2076    1.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3250   -3.1672    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5602   -1.6934    0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819   -3.2692    0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3738   -2.9562    3.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533   -4.4698    3.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2382   -4.2265    3.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  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  1  0
 15 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 23 25  1  0
 20 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  3
 29 30  1  0
 29 31  1  0
 26 32  1  0
 32 33  2  0
 12  5  1  0
 32 14  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  7 37  1  0
  8 38  1  0
 10 39  1  0
 11 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 24 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 30 56  1  0
 30 57  1  0
 30 58  1  0
 31 59  1  0
 31 60  1  0
 31 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl 2,4-dihydroxy-6-{[2-methoxy-4,5-bis(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl]oxy}benzoic acid	HMDB
Atrovirinone	MeSH

Chemical Formula

C₂₅H₂₈O₈

Average Molecular Weight

456.485

Monoisotopic Molecular Weight

456.178417872

IUPAC Name

methyl 2,4-dihydroxy-6-{[2-methoxy-4,5-bis(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl]oxy}benzoate

Traditional Name

methyl 2,4-dihydroxy-6-{[2-methoxy-4,5-bis(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl]oxy}benzoate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C(OC2=C(OC)C(=O)C(CC=C(C)C)=C(CC=C(C)C)C2=O)C=C(O)C=C1O

InChI Identifier

InChI=1S/C25H28O8/c1-13(2)7-9-16-17(10-8-14(3)4)22(29)24(23(31-5)21(16)28)33-19-12-15(26)11-18(27)20(19)25(30)32-6/h7-8,11-12,26-27H,9-10H2,1-6H3

InChI Key

AATISISCRVORPT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Ubiquinones

Alternative Parents

Substituents

Ubiquinone skeleton
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Monoterpenoid
Salicylic acid or derivatives
Aromatic monoterpenoid
Monocyclic monoterpenoid
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
P-benzoquinone
Quinone
Resorcinol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous ester
Vinylogous acid
Methyl ester
Ketone
Cyclic ketone
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036981)

Source

Endogenous

Endogenous (HMDB: HMDB0036981)

Plant

Plant (HMDB: HMDB0036981)

Animal

Animal (HMDB: HMDB0036981)

Exogenous

Food

Food (HMDB: HMDB0036981)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0036981)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036981)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036981)

Lipid metabolism pathway (HMDB: HMDB0036981)

Cellular process

Cell signaling (HMDB: HMDB0036981)

Biochemical process

Lipid transport (HMDB: HMDB0036981)

Role

Biological role

Energy source (HMDB: HMDB0036981)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036981)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	124 - 125 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0051 g/L	ALOGPS
logP	3.59	ALOGPS
logP	5.17	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	8.15	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	127.08 m³·mol⁻¹	ChemAxon
Polarizability	47.89 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	211.267	31661259
DarkChem	[M-H]-	207.334	31661259
DeepCCS	[M+H]+	207.445	30932474
DeepCCS	[M-H]-	205.049	30932474
DeepCCS	[M-2H]-	237.933	30932474
DeepCCS	[M+Na]+	213.493	30932474
AllCCS	[M+H]+	209.4	32859911
AllCCS	[M+H-H2O]+	207.1	32859911
AllCCS	[M+NH4]+	211.4	32859911
AllCCS	[M+Na]+	212.0	32859911
AllCCS	[M-H]-	213.8	32859911
AllCCS	[M+Na-2H]-	214.6	32859911
AllCCS	[M+HCOO]-	215.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.44 minutes	32390414
Predicted by Siyang on May 30, 2022	16.4147 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.68 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3438.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	241.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	206.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	154.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	79.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	779.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	766.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	75.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1421.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	665.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1566.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	529.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	200.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	177.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Atrovirinone	COC(=O)C1=C(OC2=C(OC)C(=O)C(CC=C(C)C)=C(CC=C(C)C)C2=O)C=C(O)C=C1O	5291.7	Standard polar	33892256
Atrovirinone	COC(=O)C1=C(OC2=C(OC)C(=O)C(CC=C(C)C)=C(CC=C(C)C)C2=O)C=C(O)C=C1O	2969.2	Standard non polar	33892256
Atrovirinone	COC(=O)C1=C(OC2=C(OC)C(=O)C(CC=C(C)C)=C(CC=C(C)C)C2=O)C=C(O)C=C1O	3358.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Atrovirinone,1TMS,isomer #1	COC(=O)C1=C(O)C=C(O[Si](C)(C)C)C=C1OC1=C(OC)C(=O)C(CC=C(C)C)=C(CC=C(C)C)C1=O	3245.1	Semi standard non polar	33892256
Atrovirinone,1TMS,isomer #2	COC(=O)C1=C(OC2=C(OC)C(=O)C(CC=C(C)C)=C(CC=C(C)C)C2=O)C=C(O)C=C1O[Si](C)(C)C	3196.1	Semi standard non polar	33892256
Atrovirinone,2TMS,isomer #1	COC(=O)C1=C(OC2=C(OC)C(=O)C(CC=C(C)C)=C(CC=C(C)C)C2=O)C=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C	3292.9	Semi standard non polar	33892256
Atrovirinone,1TBDMS,isomer #1	COC(=O)C1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C1OC1=C(OC)C(=O)C(CC=C(C)C)=C(CC=C(C)C)C1=O	3434.1	Semi standard non polar	33892256
Atrovirinone,1TBDMS,isomer #2	COC(=O)C1=C(OC2=C(OC)C(=O)C(CC=C(C)C)=C(CC=C(C)C)C2=O)C=C(O)C=C1O[Si](C)(C)C(C)(C)C	3383.7	Semi standard non polar	33892256
Atrovirinone,2TBDMS,isomer #1	COC(=O)C1=C(OC2=C(OC)C(=O)C(CC=C(C)C)=C(CC=C(C)C)C2=O)C=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3696.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Atrovirinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-004u-1122900000-7d0ebea1156d122370b1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Atrovirinone GC-MS (2 TMS) - 70eV, Positive	splash10-000i-1000090000-5d676f88c6dfcbcd7597	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Atrovirinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atrovirinone 10V, Positive-QTOF	splash10-0a4i-0001900000-951c621c76678ccadfa8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atrovirinone 20V, Positive-QTOF	splash10-0zg0-1105900000-01d024878898bc0f09a1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atrovirinone 40V, Positive-QTOF	splash10-0ap3-5904000000-ea441d0453210b493853	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atrovirinone 10V, Negative-QTOF	splash10-0a4i-0001900000-204b276fafbb3da002ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atrovirinone 20V, Negative-QTOF	splash10-053r-0803900000-98ef8c98bd9316ff7130	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atrovirinone 40V, Negative-QTOF	splash10-0ue9-2900000000-d8b04def57c8e306914c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atrovirinone 10V, Positive-QTOF	splash10-0pb9-0003900000-245b8efe428635033e3e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atrovirinone 20V, Positive-QTOF	splash10-0g4m-0009100000-bec6284165069fa3ab0b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atrovirinone 40V, Positive-QTOF	splash10-0ue9-2509200000-78f1511565439c560bd8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atrovirinone 10V, Negative-QTOF	splash10-0a4i-0300900000-dda47687198ffb2a9cb9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atrovirinone 20V, Negative-QTOF	splash10-00dj-0139500000-1627529caf1017ec6f83	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atrovirinone 40V, Negative-QTOF	splash10-00dl-0019200000-275359eb95e60b104f08	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015953

KNApSAcK ID

C00045676

Chemspider ID

8157073

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9981481

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

Israf DA, Tham CL, Syahida A, Lajis NH, Sulaiman MR, Mohamad AS, Zakaria ZA: Atrovirinone inhibits proinflammatory mediator synthesis through disruption of NF-kappaB nuclear translocation and MAPK phosphorylation in the murine monocytic macrophage RAW 264.7. Phytomedicine. 2010 Aug;17(10):732-9. doi: 10.1016/j.phymed.2010.02.006. Epub 2010 Apr 7. [PubMed:20378317 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Atrovirinone (HMDB0036981)

MOL for HMDB0036981 (Atrovirinone)

3D MOL for HMDB0036981 (Atrovirinone)

3D SDF for HMDB0036981 (Atrovirinone)

3D-SDF for HMDB0036981 (Atrovirinone)

PDB for HMDB0036981 (Atrovirinone)

3D PDB for HMDB0036981 (Atrovirinone)

SMILES for HMDB0036981 (Atrovirinone)

INCHI for HMDB0036981 (Atrovirinone)

Structure for HMDB0036981 (Atrovirinone)

3D Structure for HMDB0036981 (Atrovirinone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra