NP-MRD: Showing NP-Card for astrophthalide (NP0042871)

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Record Information

Version

1.0

Created at

2021-06-21 00:25:43 UTC

Updated at

2021-06-30 00:18:13 UTC

NP-MRD ID

NP0042871

Secondary Accession Numbers

None

Natural Product Identification

Common Name

astrophthalide

Provided By

JEOL Database JEOL Logo

Description

astrophthalide is found in Astrocystis sp. BCC 22166. It was first documented in 2014 (Kornsakulkarn, J., et al.). Based on a literature review very few articles have been published on methyl (3R)-7-hydroxy-3-[(1R)-1-hydroxyethyl]-1-oxo-1,3-dihydro-2-benzofuran-4-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102253D          

 30 31  0  0  0  0            999 V2000
    1.2023   -2.4398    2.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7440   -2.1662    1.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743   -0.9346    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7073   -0.0866    1.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460   -0.7229   -0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1424   -1.8019   -1.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3006   -1.5911   -2.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3345   -0.3053   -3.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7483   -0.1316   -4.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0629    0.7382   -2.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4837    0.5607   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8056    1.8917   -0.5375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1418    2.3465    0.5940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2821    3.6907    1.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855    2.4744    0.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6286    2.7924   -1.6706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358    2.1449   -2.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1789    2.6270   -3.8325 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8805   -3.4500    2.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2952   -2.4009    2.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605   -1.7348    3.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1774   -2.8232   -1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6062   -2.4351   -3.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7203    0.8249   -4.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8581    1.9434   -0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703    1.6090    1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921    3.6395    1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087    3.9945    1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2546    4.4821    0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4904    3.2092   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0  0  0  0
 17 10  1  0  0  0  0
  8  7  2  0  0  0  0
 17 18  2  0  0  0  0
 10 11  2  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
  6  5  2  0  0  0  0
 13 14  1  0  0  0  0
  5 11  1  0  0  0  0
  8  9  1  0  0  0  0
  7  6  1  0  0  0  0
  5  3  1  0  0  0  0
 10  8  1  0  0  0  0
  3  2  1  0  0  0  0
 11 12  1  0  0  0  0
  2  1  1  0  0  0  0
 12 16  1  0  0  0  0
  3  4  2  0  0  0  0
  7 23  1  0  0  0  0
  6 22  1  0  0  0  0
 12 25  1  1  0  0  0
 13 26  1  1  0  0  0
 15 30  1  0  0  0  0
 14 27  1  0  0  0  0
 14 28  1  0  0  0  0
 14 29  1  0  0  0  0
  9 24  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    1.2023   -2.4398    2.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7440   -2.1662    1.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743   -0.9346    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7073   -0.0866    1.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460   -0.7229   -0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1424   -1.8019   -1.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3006   -1.5911   -2.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3345   -0.3053   -3.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7483   -0.1316   -4.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0629    0.7382   -2.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4837    0.5607   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8056    1.8917   -0.5375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1418    2.3465    0.5940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2821    3.6907    1.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855    2.4744    0.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6286    2.7924   -1.6706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358    2.1449   -2.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1789    2.6270   -3.8325 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8805   -3.4500    2.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2952   -2.4009    2.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605   -1.7348    3.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1774   -2.8232   -1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6062   -2.4351   -3.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7203    0.8249   -4.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8581    1.9434   -0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703    1.6090    1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921    3.6395    1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087    3.9945    1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2546    4.4821    0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4904    3.2092   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 17 10  1  0
  8  7  2  0
 17 18  2  0
 10 11  2  0
 12 13  1  0
 13 15  1  0
  6  5  2  0
 13 14  1  0
  5 11  1  0
  8  9  1  0
  7  6  1  0
  5  3  1  0
 10  8  1  0
  3  2  1  0
 11 12  1  0
  2  1  1  0
 12 16  1  0
  3  4  2  0
  7 23  1  0
  6 22  1  0
 12 25  1  1
 13 26  1  1
 15 30  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
  9 24  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652306212102253D          

 30 31  0  0  0  0            999 V2000
    1.2023   -2.4398    2.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7440   -2.1662    1.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743   -0.9346    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7073   -0.0866    1.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460   -0.7229   -0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1424   -1.8019   -1.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3006   -1.5911   -2.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3345   -0.3053   -3.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7483   -0.1316   -4.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0629    0.7382   -2.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4837    0.5607   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8056    1.8917   -0.5375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1418    2.3465    0.5940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2821    3.6907    1.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855    2.4744    0.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6286    2.7924   -1.6706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358    2.1449   -2.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1789    2.6270   -3.8325 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8805   -3.4500    2.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2952   -2.4009    2.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605   -1.7348    3.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1774   -2.8232   -1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6062   -2.4351   -3.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7203    0.8249   -4.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8581    1.9434   -0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703    1.6090    1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921    3.6395    1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087    3.9945    1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2546    4.4821    0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4904    3.2092   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0  0  0  0
 17 10  1  0  0  0  0
  8  7  2  0  0  0  0
 17 18  2  0  0  0  0
 10 11  2  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
  6  5  2  0  0  0  0
 13 14  1  0  0  0  0
  5 11  1  0  0  0  0
  8  9  1  0  0  0  0
  7  6  1  0  0  0  0
  5  3  1  0  0  0  0
 10  8  1  0  0  0  0
  3  2  1  0  0  0  0
 11 12  1  0  0  0  0
  2  1  1  0  0  0  0
 12 16  1  0  0  0  0
  3  4  2  0  0  0  0
  7 23  1  0  0  0  0
  6 22  1  0  0  0  0
 12 25  1  1  0  0  0
 13 26  1  1  0  0  0
 15 30  1  0  0  0  0
 14 27  1  0  0  0  0
 14 28  1  0  0  0  0
 14 29  1  0  0  0  0
  9 24  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042871

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C(=O)OC([H])([H])[H])C2=C1C(=O)O[C@@]2([H])[C@]([H])(O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H12O6/c1-5(13)10-8-6(11(15)17-2)3-4-7(14)9(8)12(16)18-10/h3-5,10,13-14H,1-2H3/t5-,10+/m1/s1

> <INCHI_KEY>
BKNNTSDIJDLCKH-FWOIEVBISA-N

> <FORMULA>
C12H12O6

> <MOLECULAR_WEIGHT>
252.222

> <EXACT_MASS>
252.063388106

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.85938921258141

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (3R)-7-hydroxy-3-[(1R)-1-hydroxyethyl]-1-oxo-1,3-dihydro-2-benzofuran-4-carboxylate

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
1.6641018063333333

> <ALOGPS_LOGS>
-1.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.62096137927653

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.639530858947003

> <JCHEM_PKA_STRONGEST_BASIC>
-3.153743677904701

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
61.025400000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3R)-7-hydroxy-3-[(1R)-1-hydroxyethyl]-1-oxo-3H-2-benzofuran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    1.2023   -2.4398    2.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7440   -2.1662    1.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743   -0.9346    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7073   -0.0866    1.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460   -0.7229   -0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1424   -1.8019   -1.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3006   -1.5911   -2.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3345   -0.3053   -3.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7483   -0.1316   -4.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0629    0.7382   -2.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4837    0.5607   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8056    1.8917   -0.5375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1418    2.3465    0.5940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2821    3.6907    1.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855    2.4744    0.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6286    2.7924   -1.6706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358    2.1449   -2.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1789    2.6270   -3.8325 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8805   -3.4500    2.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2952   -2.4009    2.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605   -1.7348    3.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1774   -2.8232   -1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6062   -2.4351   -3.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7203    0.8249   -4.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8581    1.9434   -0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703    1.6090    1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921    3.6395    1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087    3.9945    1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2546    4.4821    0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4904    3.2092   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 17 10  1  0
  8  7  2  0
 17 18  2  0
 10 11  2  0
 12 13  1  0
 13 15  1  0
  6  5  2  0
 13 14  1  0
  5 11  1  0
  8  9  1  0
  7  6  1  0
  5  3  1  0
 10  8  1  0
  3  2  1  0
 11 12  1  0
  2  1  1  0
 12 16  1  0
  3  4  2  0
  7 23  1  0
  6 22  1  0
 12 25  1  1
 13 26  1  1
 15 30  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
  9 24  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       1.202  -2.440   2.567  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.744  -2.166   1.241  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.074  -0.935   0.786  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.707  -0.087   1.394  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.546  -0.723  -0.586  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.142  -1.802  -1.398  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.301  -1.591  -2.717  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.335  -0.305  -3.240  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.748  -0.132  -4.524  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.063   0.738  -2.425  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.484   0.561  -1.121  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.806   1.892  -0.538  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.142   2.346   0.594  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.282   3.691   1.177  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.486   2.474   0.106  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.629   2.792  -1.671  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.136   2.145  -2.762  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.179   2.627  -3.833  0.00  0.00           O+0
HETATM   19  H   UNK     0       0.881  -3.450   2.834  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.295  -2.401   2.609  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.761  -1.735   3.278  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.177  -2.823  -1.022  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.606  -2.435  -3.331  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.720   0.825  -4.741  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.858   1.943  -0.239  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.170   1.609   1.401  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.292   3.640   1.595  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.409   3.994   1.971  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.255   4.482   0.420  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.490   3.209  -0.536  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6   11    3                                                  
CONECT    6    5    7   22                                                  
CONECT    7    8    6   23                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   24                                                       
CONECT   10   17   11    8                                                  
CONECT   11   10    5   12                                                  
CONECT   12   13   11   16   25                                             
CONECT   13   12   15   14   26                                             
CONECT   14   13   27   28   29                                             
CONECT   15   13   30                                                       
CONECT   16   17   12                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    6                                                            
CONECT   23    7                                                            
CONECT   24    9                                                            
CONECT   25   12                                                            
CONECT   26   13                                                            
CONECT   27   14                                                            
CONECT   28   14                                                            
CONECT   29   14                                                            
CONECT   30   15                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

RDKit          3D

30 31  0  0  0  0  0  0  0  0999 V2000
    1.2023   -2.4398    2.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7440   -2.1662    1.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743   -0.9346    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7073   -0.0866    1.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460   -0.7229   -0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1424   -1.8019   -1.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3006   -1.5911   -2.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3345   -0.3053   -3.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7483   -0.1316   -4.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0629    0.7382   -2.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4837    0.5607   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8056    1.8917   -0.5375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1418    2.3465    0.5940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2821    3.6907    1.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855    2.4744    0.1056 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6286    2.7924   -1.6706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1358    2.1449   -2.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1789    2.6270   -3.8325 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8805   -3.4500    2.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2952   -2.4009    2.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7605   -1.7348    3.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1774   -2.8232   -1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6062   -2.4351   -3.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7203    0.8249   -4.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8581    1.9434   -0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703    1.6090    1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921    3.6395    1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087    3.9945    1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2546    4.4821    0.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4904    3.2092   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 17 10  1  0
  8  7  2  0
 17 18  2  0
 10 11  2  0
 12 13  1  0
 13 15  1  0
  6  5  2  0
 13 14  1  0
  5 11  1  0
  8  9  1  0
  7  6  1  0
  5  3  1  0
 10  8  1  0
  3  2  1  0
 11 12  1  0
  2  1  1  0
 12 16  1  0
  3  4  2  0
  7 23  1  0
  6 22  1  0
 12 25  1  1
 13 26  1  1
 15 30  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
  9 24  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl (3R)-7-hydroxy-3-[(1R)-1-hydroxyethyl]-1-oxo-1,3-dihydro-2-benzofuran-4-carboxylic acid	Generator

Chemical Formula

C₁₂H₁₂O₆

Average Mass

252.2220 Da

Monoisotopic Mass

252.06339 Da

IUPAC Name

methyl (3R)-7-hydroxy-3-[(1R)-1-hydroxyethyl]-1-oxo-1,3-dihydro-2-benzofuran-4-carboxylate

Traditional Name

methyl (3R)-7-hydroxy-3-[(1R)-1-hydroxyethyl]-1-oxo-3H-2-benzofuran-4-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C(=O)OC([H])([H])[H])C2=C1C(=O)O[C@@]2([H])[C@]([H])(O[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C12H12O6/c1-5(13)10-8-6(11(15)17-2)3-4-7(14)9(8)12(16)18-10/h3-5,10,13-14H,1-2H3/t5-,10+/m1/s1

InChI Key

BKNNTSDIJDLCKH-FWOIEVBISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Astrocystis sp. BCC 22166	JEOL database	Kornsakulkarn, J., et al. J. Tetrahedron 70, 2129 (2014)

Chemical Taxonomy

Classification

Not classified

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	0.55	ALOGPS
logP	1.66	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	61.03 m³·mol⁻¹	ChemAxon
Polarizability	23.86 Å³	ChemAxon
Number of Rings	2	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

32674848

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76900253

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kornsakulkarn, J., et al. (2014). Kornsakulkarn, J., et al. J. Tetrahedron 70, 2129 (2014). J. Tetrahedron.

Showing NP-Card for astrophthalide (NP0042871)

MOL for NP0042871 (astrophthalide)

3D MOL for NP0042871 (astrophthalide)

3D SDF for NP0042871 (astrophthalide)

3D-SDF for NP0042871 (astrophthalide)

PDB for NP0042871 (astrophthalide)

3D PDB for NP0042871 (astrophthalide)

SMILES for NP0042871 (astrophthalide)

INCHI for NP0042871 (astrophthalide)

Structure for NP0042871 (astrophthalide)

3D Structure for NP0042871 (astrophthalide)