NP-MRD: Showing NP-Card for Monascorubrin (NP0084222)

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Record Information

Version

2.0

Created at

2022-04-29 05:01:30 UTC

Updated at

2022-04-29 05:01:30 UTC

NP-MRD ID

NP0084222

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Monascorubrin

Description

Monascorubrin belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Monascorubrin is found in Monascus pilosus, Monascus purpureus, Monascus purpureus CBS 285.34, Monascus ruber and Monascus sp.. Monascorubrin was first documented in 2020 (PMID: 32872515). Based on a literature review a small amount of articles have been published on Monascorubrin (PMID: 34933631) (PMID: 33936846) (PMID: 35011300) (PMID: 33398480).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207012D          

 28 30  0  0  1  0            999 V2000
    1.1353   -0.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558   -0.2135    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5433   -0.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0953   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9238   -2.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7009    0.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2529    1.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9980    1.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5500    2.5819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570    2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9090    3.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7160    2.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2680    3.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6119    1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0599    1.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148    0.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7628   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7069   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4214   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1358   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8503   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5648   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -2.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939    0.7427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 10 14  2  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 27  2  0  0  0  0
  6 28  2  0  0  0  0
M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
    6.5192    3.0246    2.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8719    2.2827    1.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3403    1.6733    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6819    0.9185   -0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3337    0.7033   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5511   -0.0402   -1.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2353   -0.2622   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527   -1.0211   -1.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8261   -1.1676   -2.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9242   -0.5792   -1.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094   -0.8916   -1.8288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746    0.3372   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9499   -0.4732    1.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423   -1.4202    1.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4181   -1.1911    1.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3032   -0.1937    0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1136    1.2441    1.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3371    1.3911    2.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9847   -2.0179   -3.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0755   -2.3913   -3.8457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2804   -2.3183   -3.7200 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1830   -1.9667   -2.7671 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5260   -3.2391   -1.9536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4571   -1.3418   -3.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429   -1.4849   -4.3656 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2153   -0.5685   -2.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4994   -0.3464   -2.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1934    0.3704   -1.3996 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4621    2.6169    3.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2274    4.1248    2.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6364    3.0889    2.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6224    2.3653    2.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5760    1.6006    0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8868    1.1185    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7880    0.1261   -0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9015    0.9132   -0.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1696    1.1033   -0.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9388   -0.9223    1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0213    0.2973    1.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0846   -2.1013    0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6560   -2.2070    1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4399   -1.0855    2.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0214   -2.2057    1.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2167   -0.2110   -0.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3975   -0.4618    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9017    1.8213    0.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1518    1.6584    1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3538    1.3533    3.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0562    0.6654    3.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7514    2.3984    3.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -3.4346   -1.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5582   -4.0569   -2.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990   -3.1403   -1.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791   -0.7502   -3.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4 28  1  0
 28 27  1  0
 27 26  2  0
 26 24  1  0
 24 25  2  0
 24 22  1  0
 22 23  1  1
 22 21  1  0
 21 19  1  0
 19 20  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
 19  9  1  0
 22  8  1  0
 26  6  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 17 46  1  0
 17 47  1  0
 16 44  1  0
 16 45  1  0
 15 42  1  0
 15 43  1  0
 14 40  1  0
 14 41  1  0
 13 38  1  0
 13 39  1  0
 12 36  1  0
 12 37  1  0
  7 35  1  0
  5 34  1  0
 27 54  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
  3 33  1  0
  2 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END


  Mrv1652304292207012D          

 28 30  0  0  1  0            999 V2000
    1.1353   -0.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558   -0.2135    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5433   -0.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0953   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9238   -2.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7009    0.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2529    1.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9980    1.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5500    2.5819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570    2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9090    3.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7160    2.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2680    3.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6119    1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0599    1.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148    0.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7628   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7069   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4214   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1358   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8503   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5648   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -2.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939    0.7427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 10 14  2  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 27  2  0  0  0  0
  6 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084222

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)C1=C2C=C3C=C(OC=C3C(=O)[C@]2(C)OC1=O)\C=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O5/c1-4-6-7-8-9-11-19(24)20-18-13-15-12-16(10-5-2)27-14-17(15)21(25)23(18,3)28-22(20)26/h5,10,12-14H,4,6-9,11H2,1-3H3/b10-5+/t23-/m1/s1

> <INCHI_KEY>
IIPVSGPTPPURBD-HAOIVFDCSA-N

> <FORMULA>
C23H26O5

> <MOLECULAR_WEIGHT>
382.456

> <EXACT_MASS>
382.178023937

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.98236720021062

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9aR)-9a-methyl-3-octanoyl-6-[(1E)-prop-1-en-1-yl]-2H,9H,9aH-furo[3,2-g]isochromene-2,9-dione

> <ALOGPS_LOGP>
4.76

> <JCHEM_LOGP>
4.5363901769999995

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.381570371134654

> <JCHEM_PKA_STRONGEST_BASIC>
-5.241101520771261

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
110.47929999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9aR)-9a-methyl-3-octanoyl-6-[(1E)-prop-1-en-1-yl]furo[3,2-g]isochromene-2,9-dione

> <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  C   UNK     0       2.119  -0.238   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.651  -0.399   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.881  -1.732   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.911  -2.877   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.591  -4.383   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.175   1.066   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.205   2.211   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.730   3.675   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.760   4.820   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.266   4.499   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.297   5.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.803   5.324   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.834   6.468   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.742   3.035   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.712   1.890   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.188   0.426   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.157  -0.719   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.318  -2.250   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.652  -3.020   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.986  -2.250   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.319  -3.020   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.653  -2.250   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.987  -3.020   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.320  -2.250   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.654  -3.020   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.988  -2.250   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.652  -4.560   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.669   1.386   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6   17                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4                                                            
CONECT    6    2    7   28                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   10   15                                                       
CONECT   15   14    7   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    2   18                                                  
CONECT   18   17    4   19                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   19                                                            
CONECT   28    6                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆O₅

Average Mass

382.4560 Da

Monoisotopic Mass

382.17802 Da

IUPAC Name

(9aR)-9a-methyl-3-octanoyl-6-[(1E)-prop-1-en-1-yl]-2H,9H,9aH-furo[3,2-g]isochromene-2,9-dione

Traditional Name

(9aR)-9a-methyl-3-octanoyl-6-[(1E)-prop-1-en-1-yl]furo[3,2-g]isochromene-2,9-dione

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)C1=C2C=C3C=C(OC=C3C(=O)[C@]2(C)OC1=O)\C=C\C

InChI Identifier

InChI=1S/C23H26O5/c1-4-6-7-8-9-11-19(24)20-18-13-15-12-16(10-5-2)27-14-17(15)21(25)23(18,3)28-22(20)26/h5,10,12-14H,4,6-9,11H2,1-3H3/b10-5+/t23-/m1/s1

InChI Key

IIPVSGPTPPURBD-HAOIVFDCSA-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
Monascus pilosus	Fungi	KNApSAcK
Monascus purpureus	Fungi	KNApSAcK
Monascus purpureus CBS 285.34	Fungi	KNApSAcK
Monascus ruber	Fungi	KNApSAcK
Monascus sp.	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Cyclohexenone
Alpha-acyloxy ketone
2-furanone
Pyran
Dihydrofuran
Enoate ester
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4.76	ALOGPS
logP	4.54	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	19.38	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	110.48 m³·mol⁻¹	ChemAxon
Polarizability	42.98 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00053504

Chemspider ID

25046481

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12118084

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Songjanthuek P, Saleepochn T, Pluempanupat W, Yongsmith B, Kongkathip B, Wattana-Amorn P: Combination of (1)H and (13)C NMR for quantitative analysis of the orange pigments produced by Monascus kaoliang KB9. Nat Prod Res. 2021 Dec 21:1-4. doi: 10.1080/14786419.2021.2010197. [PubMed:34933631 ]
Chen S, Su DX, Gao MX, Zhang JL, Liu YB, Wu QH, Yang HL, Li L: A facile macroporous resin-based method for separation of yellow and orange Monascus pigments. Food Sci Biotechnol. 2021 Mar 8;30(4):545-553. doi: 10.1007/s10068-021-00892-1. eCollection 2021 Apr. [PubMed:33936846 ]
Tsiailanis AD, Pateraki C, Kyriazou M, Chatzigiannis CM, Chatziathanasiadou M, Parisis N, Mandala I, Tzakos AG, Koutinas A: Chemical Profiling, Bioactivity Evaluation and the Discovery of a Novel Biopigment Produced by Penicillium purpurogenum CBS 113139. Molecules. 2021 Dec 23;27(1). pii: molecules27010069. doi: 10.3390/molecules27010069. [PubMed:35011300 ]
Chen D, Wang Y, Chen M, Fan P, Li G, Wang C: Ammonium nitrate regulated the color characteristic changes of pigments in Monascus purpureus M9. AMB Express. 2021 Jan 4;11(1):3. doi: 10.1186/s13568-020-01165-6. [PubMed:33398480 ]
Li L, Chen F: Effects of mrpigG on Development and Secondary Metabolism of Monascus ruber M7. J Fungi (Basel). 2020 Aug 29;6(3). pii: jof6030156. doi: 10.3390/jof6030156. [PubMed:32872515 ]

Showing NP-Card for Monascorubrin (NP0084222)

MOL for NP0084222 (Monascorubrin)

3D MOL for NP0084222 (Monascorubrin)

3D SDF for NP0084222 (Monascorubrin)

3D-SDF for NP0084222 (Monascorubrin)

PDB for NP0084222 (Monascorubrin)

3D PDB for NP0084222 (Monascorubrin)

SMILES for NP0084222 (Monascorubrin)

INCHI for NP0084222 (Monascorubrin)

Structure for NP0084222 (Monascorubrin)

3D Structure for NP0084222 (Monascorubrin)