NP-MRD: Showing NP-Card for Rousselianone A (NP0022824)

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Record Information

Version

2.0

Created at

2021-01-06 07:59:12 UTC

Updated at

2021-07-15 17:40:05 UTC

NP-MRD ID

NP0022824

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rousselianone A

Provided By

NPAtlas

Description

Rousselianone A is found in Phaeosphaeria and Phaeosphaeria rousseliana. Rousselianone A was first documented in 1993 (PMID: 8244885). Based on a literature review very few articles have been published on 2,2,4,9-tetrahydroxy-6-methyl-7-[(3-methylbut-2-en-1-yl)oxy]-2,3-dihydro-1H-phenalene-1,3-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105373D          

 44 46  0  0  0  0            999 V2000
    5.0579   -1.9199    1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181   -0.8871    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122    0.3630    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3553   -1.0167   -0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8470    0.0270   -1.2980 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6131    0.5806   -0.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.0321   -0.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587   -1.3318   -1.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1120   -1.9144   -1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2564   -3.2521   -1.4554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -1.1355   -0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9651    0.2072   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    1.0184   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8025    2.3447    0.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7977    3.2086    0.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269    2.8916    0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    2.0982   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229    2.6959   -0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946    0.7741   -0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3882    0.4719    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4022    1.1882   -0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5750   -1.0057    0.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8507   -1.3732   -0.2685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3351   -1.3478    1.4833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5350   -1.6753   -0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8488   -2.6956   -1.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0402   -2.2485    0.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2260   -1.4406    2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -2.7611    1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6335    0.4822   -1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763    1.2185    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2121    0.3859    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203   -1.9276   -0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8225   -0.3188   -2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512    0.8302   -1.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -1.9784   -1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0106   -3.8424   -1.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7457    3.1171    0.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3473    3.9324    0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3032    2.7772   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    2.3180    0.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7780    3.7859   -0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3351   -0.5579   -0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0206   -2.0544    1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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
  9 11  2  0  0  0  0
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 16 17  1  0  0  0  0
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 17 19  2  0  0  0  0
 13 20  1  0  0  0  0
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 22 23  1  6  0  0  0
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 19  7  1  0  0  0  0
 25 11  1  0  0  0  0
 19 12  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  4 33  1  0  0  0  0
  5 34  1  0  0  0  0
  5 35  1  0  0  0  0
  8 36  1  0  0  0  0
 10 37  1  0  0  0  0
 15 38  1  0  0  0  0
 16 39  1  0  0  0  0
 18 40  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
 23 43  1  0  0  0  0
 24 44  1  0  0  0  0
M  END

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    5.0579   -1.9199    1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181   -0.8871    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122    0.3630    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3553   -1.0167   -0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8470    0.0270   -1.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131    0.5806   -0.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.0321   -0.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587   -1.3318   -1.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1120   -1.9144   -1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2564   -3.2521   -1.4554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -1.1355   -0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9651    0.2072   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    1.0184   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8025    2.3447    0.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7977    3.2086    0.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269    2.8916    0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    2.0982   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229    2.6959   -0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946    0.7741   -0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3882    0.4719    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4022    1.1882   -0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5750   -1.0057    0.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8507   -1.3732   -0.2685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3351   -1.3478    1.4833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5350   -1.6753   -0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8488   -2.6956   -1.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0402   -2.2485    0.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2260   -1.4406    2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -2.7611    1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6335    0.4822   -1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763    1.2185    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2121    0.3859    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203   -1.9276   -0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8225   -0.3188   -2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512    0.8302   -1.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -1.9784   -1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0106   -3.8424   -1.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7457    3.1171    0.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3473    3.9324    0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3032    2.7772   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    2.3180    0.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7780    3.7859   -0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3351   -0.5579   -0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0206   -2.0544    1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
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  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
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 20 22  1  0
 22 23  1  6
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 25 11  1  0
 19 12  1  0
  1 27  1  0
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 15 38  1  0
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 18 40  1  0
 18 41  1  0
 18 42  1  0
 23 43  1  0
 24 44  1  0
M  END


  Mrv1652306242105373D          

 44 46  0  0  0  0            999 V2000
    5.0579   -1.9199    1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181   -0.8871    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122    0.3630    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3553   -1.0167   -0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8470    0.0270   -1.2980 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6131    0.5806   -0.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.0321   -0.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587   -1.3318   -1.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1120   -1.9144   -1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2564   -3.2521   -1.4554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -1.1355   -0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9651    0.2072   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    1.0184   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8025    2.3447    0.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7977    3.2086    0.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269    2.8916    0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    2.0982   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229    2.6959   -0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946    0.7741   -0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3882    0.4719    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4022    1.1882   -0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5750   -1.0057    0.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8507   -1.3732   -0.2685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3351   -1.3478    1.4833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5350   -1.6753   -0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8488   -2.6956   -1.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2260   -1.4406    2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -2.7611    1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6335    0.4822   -1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763    1.2185    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2121    0.3859    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203   -1.9276   -0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8225   -0.3188   -2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512    0.8302   -1.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -1.9784   -1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0106   -3.8424   -1.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7457    3.1171    0.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3473    3.9324    0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3032    2.7772   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    2.3180    0.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7780    3.7859   -0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3351   -0.5579   -0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0206   -2.0544    1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
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 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
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 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19  7  1  0  0  0  0
 25 11  1  0  0  0  0
 19 12  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  4 33  1  0  0  0  0
  5 34  1  0  0  0  0
  5 35  1  0  0  0  0
  8 36  1  0  0  0  0
 10 37  1  0  0  0  0
 15 38  1  0  0  0  0
 16 39  1  0  0  0  0
 18 40  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
 23 43  1  0  0  0  0
 24 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022824

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C2C(OC([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])=C([H])C(O[H])=C3C(=O)C(O[H])(O[H])C(=O)C1=C23)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O7/c1-8(2)4-5-26-12-7-11(21)15-16-13(12)9(3)6-10(20)14(16)17(22)19(24,25)18(15)23/h4,6-7,20-21,24-25H,5H2,1-3H3

> <INCHI_KEY>
PPQRYVAHMXHVOC-UHFFFAOYSA-N

> <FORMULA>
C19H18O7

> <MOLECULAR_WEIGHT>
358.346

> <EXACT_MASS>
358.10525292

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.32797870882908

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2,4,9-tetrahydroxy-6-methyl-7-[(3-methylbut-2-en-1-yl)oxy]-2,3-dihydro-1H-phenalene-1,3-dione

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
3.850804055666667

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.974118597444518

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.404059398984028

> <JCHEM_PKA_STRONGEST_BASIC>
-4.912329836031719

> <JCHEM_POLAR_SURFACE_AREA>
124.28999999999999

> <JCHEM_REFRACTIVITY>
94.47919999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2,4,9-tetrahydroxy-6-methyl-7-[(3-methylbut-2-en-1-yl)oxy]phenalene-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    5.0579   -1.9199    1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181   -0.8871    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122    0.3630    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3553   -1.0167   -0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8470    0.0270   -1.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131    0.5806   -0.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.0321   -0.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587   -1.3318   -1.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1120   -1.9144   -1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2564   -3.2521   -1.4554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -1.1355   -0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9651    0.2072   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    1.0184   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8025    2.3447    0.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7977    3.2086    0.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269    2.8916    0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    2.0982   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229    2.6959   -0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946    0.7741   -0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3882    0.4719    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4022    1.1882   -0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5750   -1.0057    0.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8507   -1.3732   -0.2685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3351   -1.3478    1.4833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5350   -1.6753   -0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8488   -2.6956   -1.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0402   -2.2485    0.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2260   -1.4406    2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -2.7611    1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6335    0.4822   -1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763    1.2185    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2121    0.3859    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203   -1.9276   -0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8225   -0.3188   -2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512    0.8302   -1.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -1.9784   -1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0106   -3.8424   -1.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7457    3.1171    0.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3473    3.9324    0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3032    2.7772   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    2.3180    0.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7780    3.7859   -0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3351   -0.5579   -0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0206   -2.0544    1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 13 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  6
 22 24  1  0
 22 25  1  0
 25 26  2  0
 19  7  1  0
 25 11  1  0
 19 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  8 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 23 43  1  0
 24 44  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       5.058  -1.920   1.143  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.518  -0.887   0.241  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.312   0.363   0.049  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.355  -1.017  -0.410  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.847   0.027  -1.298  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.613   0.581  -0.969  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.388  -0.032  -0.916  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.159  -1.332  -1.208  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.112  -1.914  -1.142  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.256  -3.252  -1.455  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.183  -1.135  -0.765  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.965   0.207  -0.460  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.031   1.018  -0.070  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.803   2.345   0.233  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.798   3.209   0.627  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.527   2.892   0.158  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.458   2.098  -0.229  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.923   2.696  -0.310  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.695   0.774  -0.530  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.388   0.472   0.016  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.402   1.188  -0.022  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.575  -1.006   0.154  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.851  -1.373  -0.269  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.335  -1.348   1.483  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.535  -1.675  -0.687  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.849  -2.696  -1.315  0.00  0.00           O+0
HETATM   27  H   UNK     0       6.040  -2.248   0.723  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.226  -1.441   2.132  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.338  -2.761   1.197  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.633   0.482  -1.005  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.676   1.218   0.374  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.212   0.386   0.668  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.820  -1.928  -0.241  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.822  -0.319  -2.382  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.651   0.830  -1.347  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.942  -1.978  -1.523  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.011  -3.842  -1.468  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.746   3.117   0.773  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.347   3.932   0.395  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.303   2.777  -1.329  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.605   2.318   0.456  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.778   3.786  -0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      -6.335  -0.558  -0.568  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.021  -2.054   1.703  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   30   31   32                                             
CONECT    4    2    5   33                                                  
CONECT    5    4    6   34   35                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9   36                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   37                                                       
CONECT   11    9   12   25                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   38                                                       
CONECT   16   14   17   39                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   40   41   42                                             
CONECT   19   17    7   12                                                  
CONECT   20   13   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   25                                             
CONECT   23   22   43                                                       
CONECT   24   22   44                                                       
CONECT   25   22   26   11                                                  
CONECT   26   25                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    5                                                            
CONECT   35    5                                                            
CONECT   36    8                                                            
CONECT   37   10                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   18                                                            
CONECT   41   18                                                            
CONECT   42   18                                                            
CONECT   43   23                                                            
CONECT   44   24                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

RDKit          3D

44 46  0  0  0  0  0  0  0  0999 V2000
    5.0579   -1.9199    1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181   -0.8871    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122    0.3630    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3553   -1.0167   -0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8470    0.0270   -1.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131    0.5806   -0.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.0321   -0.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587   -1.3318   -1.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1120   -1.9144   -1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2564   -3.2521   -1.4554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -1.1355   -0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9651    0.2072   -0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    1.0184   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8025    2.3447    0.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7977    3.2086    0.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269    2.8916    0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    2.0982   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229    2.6959   -0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6946    0.7741   -0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3882    0.4719    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4022    1.1882   -0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5750   -1.0057    0.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8507   -1.3732   -0.2685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3351   -1.3478    1.4833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5350   -1.6753   -0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8488   -2.6956   -1.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0402   -2.2485    0.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2260   -1.4406    2.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -2.7611    1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6335    0.4822   -1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763    1.2185    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2121    0.3859    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203   -1.9276   -0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8225   -0.3188   -2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512    0.8302   -1.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418   -1.9784   -1.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0106   -3.8424   -1.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7457    3.1171    0.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3473    3.9324    0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3032    2.7772   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    2.3180    0.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7780    3.7859   -0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3351   -0.5579   -0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0206   -2.0544    1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 13 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  6
 22 24  1  0
 22 25  1  0
 25 26  2  0
 19  7  1  0
 25 11  1  0
 19 12  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  8 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 23 43  1  0
 24 44  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2,2,4,9-Tetrahydroxy-6-isopentenoxy-7-methyl-1H-phenalene-1,3(2H)-dione	MeSH

Chemical Formula

C₁₉H₁₈O₇

Average Mass

358.3460 Da

Monoisotopic Mass

358.10525 Da

IUPAC Name

2,2,4,9-tetrahydroxy-6-methyl-7-[(3-methylbut-2-en-1-yl)oxy]-2,3-dihydro-1H-phenalene-1,3-dione

Traditional Name

2,2,4,9-tetrahydroxy-6-methyl-7-[(3-methylbut-2-en-1-yl)oxy]phenalene-1,3-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CCOC1=CC(O)=C2C(=O)C(O)(O)C(=O)C3=C(O)C=C(C)C1=C23

InChI Identifier

InChI=1S/C19H18O7/c1-8(2)4-5-26-12-7-11(21)15-16-13(12)9(3)6-10(20)14(16)17(22)19(24,25)18(15)23/h4,6-7,20-21,24-25H,5H2,1-3H3

InChI Key

PPQRYVAHMXHVOC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phaeosphaeria	NPAtlas	8244885
Phaeosphaeria rousseliana	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as phenalanes. These are aromatic hydrocarbons containing a cyclohexene ring fused to both benzenes of a naphthalene ring system, so as to form a triad.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenalanes

Sub Class

Not Available

Direct Parent

Phenalanes

Alternative Parents

Substituents

Phenalane
2-naphthol
Naphthalene
Phenol ether
Aryl ketone
Aryl alkyl ketone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Polyol
Ether
Carbonyl hydrate
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.85	ALOGPS
logP	3.85	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.4	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.48 m³·mol⁻¹	ChemAxon
Polarizability	36.33 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

External Links

NPAtlas ID

NPA011362

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78435361

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101656818

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xiao JZ, Kumazawa S, Tomita H, Yoshikawa N, Kimura C, Mikawa T: Rousselianone A, novel antibiotic related to phenalenone produced by Phaeosphaeria rousseliana. J Antibiot (Tokyo). 1993 Oct;46(10):1570-4. doi: 10.7164/antibiotics.46.1570. [PubMed:8244885 ]

Showing NP-Card for Rousselianone A (NP0022824)

MOL for NP0022824 (Rousselianone A)

3D MOL for NP0022824 (Rousselianone A)

3D SDF for NP0022824 (Rousselianone A)

3D-SDF for NP0022824 (Rousselianone A)

PDB for NP0022824 (Rousselianone A)

3D PDB for NP0022824 (Rousselianone A)

SMILES for NP0022824 (Rousselianone A)

INCHI for NP0022824 (Rousselianone A)

Structure for NP0022824 (Rousselianone A)

3D Structure for NP0022824 (Rousselianone A)