NP-MRD: Showing NP-Card for 7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid (NP0326786)

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Record Information

Version

2.0

Created at

2022-09-12 08:43:28 UTC

Updated at

2022-09-12 08:43:28 UTC

NP-MRD ID

NP0326786

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid

Description

7-{8A-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-6,7,8,8a-tetrahydro-1H-isochromen-3-yl}hepta-2,4,6-trienoic acid belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid is found in Penicillium canescens. Based on a literature review very few articles have been published on 7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-6,7,8,8a-tetrahydro-1H-isochromen-3-yl}hepta-2,4,6-trienoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122210432D          

 47 49  0  0  0  0            999 V2000
   -3.0657    3.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532    3.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7229    2.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105    2.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802    2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    2.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    2.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    3.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461    4.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764    4.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889    4.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711    4.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835    3.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138    4.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1263    4.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4085    3.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2209    3.4444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782    2.9556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663    4.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966    3.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8091    3.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0913    4.7337    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.3394    3.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1519    3.4697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    2.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697    2.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007    0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6296    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3441    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6296    0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    2.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    1.6327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6623    1.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1320    0.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142   -0.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6804    0.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748    1.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570    0.4277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051    1.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8176    1.6917    0.0000 O   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
  3  4  2  0  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  4  0  0  0
 11 12  2  0  0  0  0
 13 12  1  4  0  0  0
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 31 32  1  0  0  0  0
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 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 26 38  1  0  0  0  0
  7 38  1  0  0  0  0
 38 39  2  0  0  0  0
  5 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
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 40 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
  3 46  1  0  0  0  0
 46 47  1  0  0  0  0
M  END

     RDKit          3D

 82 84  0  0  0  0  0  0  0  0999 V2000
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    3.8792   -4.5508    4.2880 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6352   -4.4822    3.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7972   -3.6271    2.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4611   -3.5820    1.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3286   -1.5983   -0.3495 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2412   -2.7018   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0331    0.1763   -0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5894   -0.4742    0.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1455    1.4272   -0.6444 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3716    1.5408    0.6831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1241    1.8079   -1.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4964    1.9203   -1.1036 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5316    3.1149   -0.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9537    6.6866   -3.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1782   -3.3990   -2.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8235   -4.2323   -1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4059   -7.2234    2.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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 47 82  1  0
M  END


  Mrv1652309122210432D          

 47 49  0  0  0  0            999 V2000
   -3.0657    3.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532    3.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3802    2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    2.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    2.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    3.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461    4.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764    4.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889    4.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9711    4.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835    3.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138    4.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1263    4.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4085    3.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2209    3.4444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782    2.9556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663    4.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966    3.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8091    3.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0913    4.7337    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.3394    3.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1519    3.4697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    2.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8697    2.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717    0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007    0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6296    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3441    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6296    0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    2.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    1.6327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6623    1.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1320    0.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142   -0.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6804    0.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748    1.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570    0.4277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051    1.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8176    1.6917    0.0000 O   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
  3  4  2  0  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  4  0  0  0
 11 12  2  0  0  0  0
 13 12  1  4  0  0  0
 13 14  2  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 10 20  2  0  0  0  0
 20 21  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 26 38  1  0  0  0  0
  7 38  1  0  0  0  0
 38 39  2  0  0  0  0
  5 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 40 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
  3 46  1  0  0  0  0
 46 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326786

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CC23COC(C=CC=CC=CC(O)=O)=CC2=C(Br)C(=O)C(C)(OC(=O)CC(O)CC(C)O)C3=O)=C(C(C)=O)C(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C33H35BrO13/c1-17(35)11-20(37)13-25(40)47-32(3)30(43)27(34)22-14-21(9-7-5-6-8-10-24(38)39)46-16-33(22,31(32)44)15-19-12-23(45-4)28(41)29(42)26(19)18(2)36/h5-10,12,14,17,20,35,37,41-42H,11,13,15-16H2,1-4H3,(H,38,39)

> <INCHI_KEY>
HZAFGTDVJZNBOD-UHFFFAOYSA-N

> <FORMULA>
C33H35BrO13

> <MOLECULAR_WEIGHT>
719.534

> <EXACT_MASS>
718.126104

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
67.96280021862782

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-6,7,8,8a-tetrahydro-1H-isochromen-3-yl}hepta-2,4,6-trienoic acid

> <JCHEM_LOGP>
2.988824582666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.12954435798366

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.469083233232219

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5453013041240222

> <JCHEM_POLAR_SURFACE_AREA>
214.19

> <JCHEM_REFRACTIVITY>
176.44920000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1H-isochromen-3-yl}hepta-2,4,6-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.723   5.785   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.206   6.052   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.216   4.872   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.700   5.140   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.710   3.960   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.807   4.227   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   5.675   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.183   5.407   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.173   6.587   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.646   8.034   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.636   9.214   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.153   8.946   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.679   7.499   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.196   7.232   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.186   8.411   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.702   8.144   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.229   6.697   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.746   6.429   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -7.239   5.517   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.870   8.301   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.860   7.122   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.377   7.389   0.000  0.00  0.00           C+0
HETATM   23 Br   UNK     0       3.904   8.836   0.000  0.00  0.00          Br+0
HETATM   24  C   UNK     0       4.367   6.209   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.883   6.477   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.840   4.762   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.357   4.495   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.840   3.222   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.174   2.452   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.174   0.912   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.508   3.222   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.841   2.452   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.841   0.912   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.175   3.222   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.509   2.452   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.842   3.222   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      10.509   0.912   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.324   4.495   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.797   3.048   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.236   2.513   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.246   1.333   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.773  -0.114   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.270   1.601   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -2.753   2.245   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -3.280   0.798   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -3.743   3.425   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -5.259   3.158   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   46                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   40                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   21   38                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   10   21                                                       
CONECT   21   20    7   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   38                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   26    7   39                                                  
CONECT   39   38                                                            
CONECT   40    5   41   44                                                  
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   40   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44    3   47                                                  
CONECT   47   46                                                            
MASTER        0    0    0    0    0    0    0    0   47    0   98    0
END

View in JSmol

Synonyms

Value	Source
7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-6,7,8,8a-tetrahydro-1H-isochromen-3-yl}hepta-2,4,6-trienoate	Generator

Chemical Formula

C₃₃H₃₅BrO₁₃

Average Mass

719.5340 Da

Monoisotopic Mass

718.12610 Da

IUPAC Name

7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-6,7,8,8a-tetrahydro-1H-isochromen-3-yl}hepta-2,4,6-trienoic acid

Traditional Name

7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1H-isochromen-3-yl}hepta-2,4,6-trienoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(CC23COC(C=CC=CC=CC(O)=O)=CC2=C(Br)C(=O)C(C)(OC(=O)CC(O)CC(C)O)C3=O)=C(C(C)=O)C(O)=C1O

InChI Identifier

InChI=1S/C33H35BrO13/c1-17(35)11-20(37)13-25(40)47-32(3)30(43)27(34)22-14-21(9-7-5-6-8-10-24(38)39)46-16-33(22,31(32)44)15-19-12-23(45-4)28(41)29(42)26(19)18(2)36/h5-10,12,14,17,20,35,37,41-42H,11,13,15-16H2,1-4H3,(H,38,39)

InChI Key

HZAFGTDVJZNBOD-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Penicillium canescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Azaphilone
Methoxyphenol
Acetophenone
Phenoxy compound
Methoxybenzene
Aryl alkyl ketone
Phenol ether
Catechol
Benzoyl
Anisole
1-hydroxy-4-unsubstituted benzenoid
Cyclohexenone
Alpha-acyloxy ketone
Phenol
Fatty acid ester
Beta-hydroxy acid
Alkyl aryl ether
Fatty acyl
Benzenoid
Hydroxy acid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha-haloketone
Vinylogous acid
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Oxacycle
Bromoalkene
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl bromide
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organobromide
Organohalogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.99	ChemAxon
pKa (Strongest Acidic)	4.47	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	214.19 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	176.45 m³·mol⁻¹	ChemAxon
Polarizability	67.96 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162814103

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid (NP0326786)

MOL for NP0326786 (7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid)

3D MOL for NP0326786 (7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid)

3D SDF for NP0326786 (7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid)

3D-SDF for NP0326786 (7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid)

PDB for NP0326786 (7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid)

3D PDB for NP0326786 (7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid)

SMILES for NP0326786 (7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid)

INCHI for NP0326786 (7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid)

Structure for NP0326786 (7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid)

3D Structure for NP0326786 (7-{8a-[(2-acetyl-3,4-dihydroxy-5-methoxyphenyl)methyl]-5-bromo-7-[(3,5-dihydroxyhexanoyl)oxy]-7-methyl-6,8-dioxo-1h-isochromen-3-yl}hepta-2,4,6-trienoic acid)