NP-MRD: Showing NP-Card for Alternariol (NP0004741)

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Record Information

Version

2.0

Created at

2020-12-09 02:09:44 UTC

Updated at

2021-08-19 23:59:35 UTC

NP-MRD ID

NP0004741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Alternariol

Provided By

NPAtlas

Description

Alternariol, also known as AOH, belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Alternariol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Alternariol is found in Adenocarpus foliolosus, Alternaria, Alternaria alternata, Alternaria porri, Carica papaya and Maytenus hookeri. Alternariol was first documented in 1953 (PMID: 13105649). Based on a literature review a small amount of articles have been published on Alternariol (PMID: 15822993) (PMID: 16464542) (PMID: 18727009) (PMID: 19530709).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118093D          

 29 31  0  0  0  0            999 V2000
   -1.3192    2.1549   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084    0.7410   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632    0.3253   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3461   -0.9691    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6895   -1.3287    0.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3892   -1.9228    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463   -1.5842    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576   -2.5331    0.2677 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1244   -2.3137    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9145   -3.2729    0.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -1.0177    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -0.8095    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066   -1.7851    0.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834    0.5170   -0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5057    1.5313   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9161    2.8647   -0.4686 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169    1.3201   -0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6799    0.0409   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -0.2505   -0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0933    2.5619   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208    2.6872    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3743    2.6615   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7043    1.1050   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1887   -1.3460    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6353   -2.9772    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9487   -2.7320    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    0.6796   -0.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680    3.4841    0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5561    2.1677   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  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  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19  2  1  0  0  0  0
 19  7  2  0  0  0  0
 18 11  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 23  1  0  0  0  0
  5 24  1  0  0  0  0
  6 25  1  0  0  0  0
 13 26  1  0  0  0  0
 14 27  1  0  0  0  0
 16 28  1  0  0  0  0
 17 29  1  0  0  0  0
M  END

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.3192    2.1549   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084    0.7410   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632    0.3253   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3461   -0.9691    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6895   -1.3287    0.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3892   -1.9228    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463   -1.5842    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576   -2.5331    0.2677 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1244   -2.3137    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9145   -3.2729    0.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -1.0177    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -0.8095    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066   -1.7851    0.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834    0.5170   -0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5057    1.5313   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9161    2.8647   -0.4686 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169    1.3201   -0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6799    0.0409   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -0.2505   -0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0933    2.5619   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208    2.6872    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3743    2.6615   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7043    1.1050   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1887   -1.3460    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6353   -2.9772    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9487   -2.7320    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    0.6796   -0.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680    3.4841    0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5561    2.1677   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 19  7  2  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
M  END


  Mrv1652306242118093D          

 29 31  0  0  0  0            999 V2000
   -1.3192    2.1549   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084    0.7410   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632    0.3253   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3461   -0.9691    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6895   -1.3287    0.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3892   -1.9228    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463   -1.5842    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576   -2.5331    0.2677 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1244   -2.3137    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9145   -3.2729    0.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -1.0177    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -0.8095    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066   -1.7851    0.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834    0.5170   -0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5057    1.5313   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9161    2.8647   -0.4686 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169    1.3201   -0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6799    0.0409   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -0.2505   -0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0933    2.5619   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208    2.6872    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3743    2.6615   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7043    1.1050   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1887   -1.3460    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6353   -2.9772    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9487   -2.7320    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    0.6796   -0.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680    3.4841    0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5561    2.1677   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  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  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19  2  1  0  0  0  0
 19  7  2  0  0  0  0
 18 11  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 23  1  0  0  0  0
  5 24  1  0  0  0  0
  6 25  1  0  0  0  0
 13 26  1  0  0  0  0
 14 27  1  0  0  0  0
 16 28  1  0  0  0  0
 17 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004741

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)OC3=C(C2=C1[H])C(=C([H])C(O[H])=C3[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3

> <INCHI_KEY>
CEBXXEKPIIDJHL-UHFFFAOYSA-N

> <FORMULA>
C14H10O5

> <MOLECULAR_WEIGHT>
258.2262

> <EXACT_MASS>
258.05282343

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.13868270042601

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7,9-trihydroxy-1-methyl-6H-benzo[c]chromen-6-one

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
3.1780528656666664

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.507964495567593

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.630330073955936

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0253299520481045

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
67.92300000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alternariol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.3192    2.1549   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084    0.7410   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632    0.3253   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3461   -0.9691    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6895   -1.3287    0.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3892   -1.9228    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463   -1.5842    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576   -2.5331    0.2677 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1244   -2.3137    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9145   -3.2729    0.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -1.0177    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -0.8095    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066   -1.7851    0.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834    0.5170   -0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5057    1.5313   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9161    2.8647   -0.4686 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169    1.3201   -0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6799    0.0409   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -0.2505   -0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0933    2.5619   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208    2.6872    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3743    2.6615   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7043    1.1050   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1887   -1.3460    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6353   -2.9772    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9487   -2.7320    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    0.6796   -0.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680    3.4841    0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5561    2.1677   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 19  7  2  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  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      -1.319   2.155  -0.300  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.608   0.741  -0.172  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.963   0.325  -0.132  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.346  -0.969   0.031  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.689  -1.329   0.063  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.389  -1.923   0.165  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.046  -1.584   0.134  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.158  -2.533   0.268  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.124  -2.314   0.252  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.915  -3.273   0.388  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.594  -1.018   0.085  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.956  -0.810   0.057  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.907  -1.785   0.196  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.383   0.517  -0.132  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.506   1.531  -0.278  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.916   2.865  -0.469  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.117   1.320  -0.249  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.680   0.041  -0.064  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.681  -0.251  -0.036  0.00  0.00           C+0
HETATM   20  H   UNK     0      -1.093   2.562  -1.301  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.921   2.687   0.597  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.374   2.662  -0.219  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.704   1.105  -0.244  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.189  -1.346   0.955  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.635  -2.977   0.299  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.949  -2.732   0.332  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.447   0.680  -0.153  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.068   3.484   0.325  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.556   2.168  -0.397  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1    3   19                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   24                                                       
CONECT    6    4    7   25                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   26                                                       
CONECT   14   12   15   27                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   28                                                       
CONECT   17   15   18   29                                                  
CONECT   18   17   19   11                                                  
CONECT   19   18    2    7                                                  
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26   13                                                            
CONECT   27   14                                                            
CONECT   28   16                                                            
CONECT   29   17                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

RDKit          3D

29 31  0  0  0  0  0  0  0  0999 V2000
   -1.3192    2.1549   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084    0.7410   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9632    0.3253   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3461   -0.9691    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6895   -1.3287    0.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3892   -1.9228    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0463   -1.5842    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576   -2.5331    0.2677 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1244   -2.3137    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9145   -3.2729    0.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -1.0177    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -0.8095    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066   -1.7851    0.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834    0.5170   -0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5057    1.5313   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9161    2.8647   -0.4686 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169    1.3201   -0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6799    0.0409   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -0.2505   -0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0933    2.5619   -1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208    2.6872    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3743    2.6615   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7043    1.1050   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1887   -1.3460    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6353   -2.9772    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9487   -2.7320    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    0.6796   -0.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680    3.4841    0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5561    2.1677   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 19  7  2  0
 18 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
 13 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3,4',5-Trihydroxy-6'-methyldibenzo-alpha-pyrone	ChEBI
3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylic acid gamma-lactone	ChEBI
AOH	ChEBI
3,4',5-Trihydroxy-6'-methyldibenzo-a-pyrone	Generator
3,4',5-Trihydroxy-6'-methyldibenzo-α-pyrone	Generator
3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylate g-lactone	Generator
3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylate gamma-lactone	Generator
3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylate γ-lactone	Generator
3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylic acid g-lactone	Generator
3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylic acid γ-lactone	Generator
1-Methyl-3,7,9-trihydroxy-6H-dibenzo(b,D)pyran-6-one	HMDB
3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one	HMDB
3,7,9-Trihydroxy-1-methyl-6H-dibenzo(b,D)pyran-6-one	HMDB
3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,D]pyran-6-one	HMDB
3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,D]pyran-6-one, 9ci	HMDB
Alternariol 3,4',5-trihydroxy-6'-methyl-dibenzo[a]pyrone	HMDB
Alternariol from alternaria sp.	HMDB

Chemical Formula

C₁₄H₁₀O₅

Average Mass

258.2262 Da

Monoisotopic Mass

258.05282 Da

IUPAC Name

3,7,9-trihydroxy-1-methyl-6H-benzo[c]chromen-6-one

Traditional Name

alternariol

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC2=C1C1=CC(O)=CC(O)=C1C(=O)O2

InChI Identifier

InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3

InChI Key

CEBXXEKPIIDJHL-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
Adenocarpus foliolosus	LOTUS Database	35616633
Alternaria	NPAtlas	13105649
Alternaria alternata	LOTUS Database	35616633
Alternaria porri	LOTUS Database	35616633
Carica papaya	KNApSAcK Database	22123792
Carica papaya L.	Plant	KNApSAcK
Maytenus hookeri	LOTUS Database	35616633
Passiflora spp.	KNApSAcK Database	22123792

Species Where Detected

Species Name	Source	Reference
Alternaria cucumerina	KNApSAcK Database	22123792
Alternaria dauci	KNApSAcK Database	22123792
Alternaria tenuis NRRL 5255	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Not Available

Substituents

Not Available

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	61.89 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.49	ALOGPS
logP	3.18	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.63	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.92 m³·mol⁻¹	ChemAxon
Polarizability	25.14 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

NPA020438

HMDB ID

HMDB0030831

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alternariol

METLIN ID

Not Available

PubChem Compound

5359485

PDB ID

Not Available

ChEBI ID

64983

Good Scents ID

rw1701901

References

General References

RAISTRICK H, STICKINGS CE, THOMAS R: Studies in the biochemistry of microorganisms. 90. Alternariol and alternariol monomethyl ether, metabolic products of Alternaria tenuis. Biochem J. 1953 Oct;55(3):421-33. doi: 10.1042/bj0550421. [PubMed:13105649 ]
Koch K, Podlech J, Pfeiffer E, Metzler M: Total synthesis of alternariol. J Org Chem. 2005 Apr 15;70(8):3275-6. doi: 10.1021/jo050075r. [PubMed:15822993 ]
Brugger EM, Wagner J, Schumacher DM, Koch K, Podlech J, Metzler M, Lehmann L: Mutagenicity of the mycotoxin alternariol in cultured mammalian cells. Toxicol Lett. 2006 Jul 14;164(3):221-30. doi: 10.1016/j.toxlet.2006.01.001. Epub 2006 Feb 7. [PubMed:16464542 ]
Fehr M, Pahlke G, Fritz J, Christensen MO, Boege F, Altemoller M, Podlech J, Marko D: Alternariol acts as a topoisomerase poison, preferentially affecting the IIalpha isoform. Mol Nutr Food Res. 2009 Apr;53(4):441-51. doi: 10.1002/mnfr.200700379. [PubMed:18727009 ]
Asam S, Konitzer K, Schieberle P, Rychlik M: Stable isotope dilution assays of alternariol and alternariol monomethyl ether in beverages. J Agric Food Chem. 2009 Jun 24;57(12):5152-60. doi: 10.1021/jf900450w. [PubMed:19530709 ]

Showing NP-Card for Alternariol (NP0004741)

MOL for NP0004741 (Alternariol)

3D MOL for NP0004741 (Alternariol)

3D SDF for NP0004741 (Alternariol)

3D-SDF for NP0004741 (Alternariol)

PDB for NP0004741 (Alternariol)

3D PDB for NP0004741 (Alternariol)

SMILES for NP0004741 (Alternariol)

INCHI for NP0004741 (Alternariol)

Structure for NP0004741 (Alternariol)

3D Structure for NP0004741 (Alternariol)