NP-MRD: Showing NP-Card for (+)-Mitorubrinic acid (NP0083652)

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Record Information

Version

2.0

Created at

2022-04-29 04:37:30 UTC

Updated at

2022-04-29 04:37:30 UTC

NP-MRD ID

NP0083652

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Mitorubrinic acid

Description

Mitorubrinic acid, (S)- belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center. (+)-Mitorubrinic acid is found in Hypoxylon fragiforme, Penicillium porrecta, Pyrenomyxa invocans, Penicillium funiculosum, Penicillium rubrum, Tessaracoccus austrocalifornicus, Tessaracoccus convolutes, Tessaracoccus flavus, Tessaracoccus macrosporus, Tessaracoccus mimosinus, Tessaracoccus udagawae and Tessaracoccus wortmannii. (+)-Mitorubrinic acid was first documented in 2006 (PMID: 16869640). Based on a literature review a small amount of articles have been published on Mitorubrinic acid, (S)- (PMID: 25591039) (PMID: 28608842) (PMID: 26529013) (PMID: 23094121).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206372D          

 30 32  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0980   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -2.0127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802   -2.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6623   -2.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1320   -3.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142   -4.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2267   -4.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5088   -5.2570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570   -3.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748   -3.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -2.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6804   -3.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105   -1.5240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  1  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  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 15  1  0  0  0  0
  6 16  2  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
   -3.1846   -0.4129   -2.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2981   -0.0757   -1.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5585    0.2127   -1.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5908    0.5263   -0.9842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8834    0.8248   -1.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3305    0.5432    0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0668    0.2541    0.8725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7904    0.2669    2.2274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0321   -0.0600    0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6976   -0.3669    0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5142   -0.3364    1.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6211   -0.6862   -0.2534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.9858    0.1800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2734   -2.1874    1.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4590   -1.3621   -1.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1292   -1.8765   -2.0103 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8925   -1.1540   -1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5448   -0.3730   -0.3314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838   -0.1851   -0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6163    0.6152    0.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0634    0.8170    0.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167    1.6116    1.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1413    1.8303    1.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7089    2.5893    1.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8690    1.1965    0.0222 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8766    1.2588    1.3729 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5058    1.0990    1.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7962    0.3202    0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    0.1396    0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2428    0.9798    1.5935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3623    0.3278   -2.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5701   -0.3886   -3.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8440   -1.4571   -2.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7562    0.1967   -2.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5657    0.0672   -1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1138    0.7838    1.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5574    0.4997    2.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648   -3.0291    0.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6418   -1.9895    2.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8122   -2.4534    1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4370   -1.6733   -1.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5116   -0.7016   -1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5980    0.3126   -0.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319    2.0990    1.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7451    0.7577    0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9627    1.6247    2.3191 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
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 13 12  1  6
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 25  1  0
 23 24  2  0
  9  2  1  0
 29 13  1  0
 28 18  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  5 35  1  0
  6 36  1  0
  8 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 17 41  1  0
 19 42  1  0
 27 46  1  0
 21 43  1  0
 22 44  1  0
 25 45  1  0
M  END


  Mrv1652304292206372D          

 30 32  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0980   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -2.0127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802   -2.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6623   -2.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1320   -3.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142   -4.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2267   -4.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5088   -5.2570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570   -3.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748   -3.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -2.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6804   -3.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105   -1.5240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  1  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  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 15  1  0  0  0  0
  6 16  2  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0083652

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=CC(O)=C1C(=O)O[C@@]1(C)C(=O)C=C2C=C(OC=C2C1=O)\C=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H16O9/c1-10-5-12(22)8-15(23)18(10)20(28)30-21(2)16(24)7-11-6-13(3-4-17(25)26)29-9-14(11)19(21)27/h3-9,22-23H,1-2H3,(H,25,26)/b4-3+/t21-/m0/s1

> <INCHI_KEY>
ZJIWQCFXEQSFGR-SHTLVRLNSA-N

> <FORMULA>
C21H16O9

> <MOLECULAR_WEIGHT>
412.35

> <EXACT_MASS>
412.079432095

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
38.578551740012045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[(7S)-7-(2,4-dihydroxy-6-methylbenzoyloxy)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-3-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
3.2163820356666664

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.682542165482499

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.845176395681081

> <JCHEM_PKA_STRONGEST_BASIC>
-4.003837043621403

> <JCHEM_POLAR_SURFACE_AREA>
147.43

> <JCHEM_REFRACTIVITY>
106.20949999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[(7S)-7-(2,4-dihydroxy-6-methylbenzoyloxy)-7-methyl-6,8-dioxoisochromen-3-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.183  -2.043   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.807  -3.757   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.710  -4.025   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.236  -5.472   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.246  -6.651   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.773  -8.099   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.290  -8.366   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.816  -9.813   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.280  -7.186   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.753  -5.739   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.743  -4.559   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.270  -6.384   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.700  -2.845   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5   29                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13                                                            
CONECT   15    8                                                            
CONECT   16    6                                                            
CONECT   17    2   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   20   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   18   29                                                  
CONECT   29   28    3   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
Mitorubrinic acid	MeSH

Chemical Formula

C₂₁H₁₆O₉

Average Mass

412.3500 Da

Monoisotopic Mass

412.07943 Da

IUPAC Name

(2E)-3-[(7S)-7-(2,4-dihydroxy-6-methylbenzoyloxy)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-3-yl]prop-2-enoic acid

Traditional Name

(2E)-3-[(7S)-7-(2,4-dihydroxy-6-methylbenzoyloxy)-7-methyl-6,8-dioxoisochromen-3-yl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC(O)=C1C(=O)O[C@@]1(C)C(=O)C=C2C=C(OC=C2C1=O)\C=C\C(O)=O

InChI Identifier

InChI=1S/C21H16O9/c1-10-5-12(22)8-15(23)18(10)20(28)30-21(2)16(24)7-11-6-13(3-4-17(25)26)29-9-14(11)19(21)27/h3-9,22-23H,1-2H3,(H,25,26)/b4-3+/t21-/m0/s1

InChI Key

ZJIWQCFXEQSFGR-SHTLVRLNSA-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
Hypoxylon fragiforme	Fungi	KNApSAcK
Penicillium porrecta	Fungi	KNApSAcK
Pyrenomyxa invocans	-	KNApSAcK
Talaromyces funiculosus	Fungi	KNApSAcK
Talaromyces ruber	Fungi	KNApSAcK
Tessaracoccus austrocalifornicus	-	KNApSAcK
Tessaracoccus convolutes	-	KNApSAcK
Tessaracoccus flavus	-	KNApSAcK
Tessaracoccus macrosporus	-	KNApSAcK
Tessaracoccus mimosinus	-	KNApSAcK
Tessaracoccus udagawae	-	KNApSAcK
Tessaracoccus wortmannii	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaphilones

Sub Class

Not Available

Direct Parent

Azaphilones

Alternative Parents

Substituents

Azaphilone
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Benzoate ester
Salicylic acid or derivatives
Benzoic acid or derivatives
M-cresol
Benzoyl
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Phenol
Toluene
Monocyclic benzene moiety
Pyran
Benzenoid
Vinylogous acid
Vinylogous ester
Carboxylic acid ester
Ketone
Cyclic ketone
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	2.58	ALOGPS
logP	3.22	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.85	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	147.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	106.21 m³·mol⁻¹	ChemAxon
Polarizability	38.58 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00052480

Chemspider ID

57301884

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24721422

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xiao Z, Lin S, Tan C, Lu Y, He L, Huang X, She Z: Asperlones A and B, dinaphthalenone derivatives from a mangrove endophytic fungus Aspergillus sp. 16-5C. Mar Drugs. 2015 Jan 13;13(1):366-78. doi: 10.3390/md13010366. [PubMed:25591039 ]
Lau SKP, Tsang CC, Woo PCY: Talaromyces marneffei Genomic, Transcriptomic, Proteomic and Metabolomic Studies Reveal Mechanisms for Environmental Adaptations and Virulence. Toxins (Basel). 2017 Jun 13;9(6). pii: toxins9060192. doi: 10.3390/toxins9060192. [PubMed:28608842 ]
Tam EW, Tsang CC, Lau SK, Woo PC: Polyketides, toxins and pigments in Penicillium marneffei. Toxins (Basel). 2015 Oct 30;7(11):4421-36. doi: 10.3390/toxins7114421. [PubMed:26529013 ]
Woo PC, Lam CW, Tam EW, Leung CK, Wong SS, Lau SK, Yuen KY: First discovery of two polyketide synthase genes for mitorubrinic acid and mitorubrinol yellow pigment biosynthesis and implications in virulence of Penicillium marneffei. PLoS Negl Trop Dis. 2012;6(10):e1871. doi: 10.1371/journal.pntd.0001871. Epub 2012 Oct 18. [PubMed:23094121 ]
Marsini MA, Gowin KM, Pettus TR: Total synthesis of (+/-)-mitorubrinic acid. Org Lett. 2006 Aug 3;8(16):3481-3. doi: 10.1021/ol0610993. [PubMed:16869640 ]

Showing NP-Card for (+)-Mitorubrinic acid (NP0083652)

MOL for NP0083652 ((+)-Mitorubrinic acid)

3D MOL for NP0083652 ((+)-Mitorubrinic acid)

3D SDF for NP0083652 ((+)-Mitorubrinic acid)

3D-SDF for NP0083652 ((+)-Mitorubrinic acid)

PDB for NP0083652 ((+)-Mitorubrinic acid)

3D PDB for NP0083652 ((+)-Mitorubrinic acid)

SMILES for NP0083652 ((+)-Mitorubrinic acid)

INCHI for NP0083652 ((+)-Mitorubrinic acid)

Structure for NP0083652 ((+)-Mitorubrinic acid)

3D Structure for NP0083652 ((+)-Mitorubrinic acid)