NP-MRD: Showing NP-Card for Monascin (NP0071507)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 16:52:58 UTC

Updated at

2022-04-28 16:52:58 UTC

NP-MRD ID

NP0071507

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Monascin

Description

Monascin, also known as monascusone b, belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Monascin 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. Monascin is found in Monascus kaoliang, Monascus pilosus, Monascus purpureus Mentii and Monascus spp.. Monascin was first documented in 2021 (PMID: 34408740). Based on a literature review a significant number of articles have been published on monascin (PMID: 35353924) (PMID: 35284245) (PMID: 34933631) (PMID: 34684882) (PMID: 34265877) (PMID: 34108955).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218522D          

 26 28  0  0  1  0            999 V2000
   -1.2950   -0.0168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430   -0.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3190    0.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401    0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0219    1.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5302    2.3371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288    1.8955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3809    1.2824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1259    0.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1345    1.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0483    2.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6614    2.9905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2413    2.6100    0.0000 O   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
    2.8490    0.3805    0.0000 O   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
    0.3439    2.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979   -1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049   -1.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0598   -2.3706    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  9 15  1  0  0  0  0
 12 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 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
  9 23  1  1  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
   -8.1438   -0.3549    2.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0069   -0.4372    1.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8053    0.0048    1.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7331   -0.1236    0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4930    0.2880    0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4336    0.1631    0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7233   -0.3855   -1.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1337   -0.4008   -1.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9778   -0.6916   -0.4715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -0.9520   -2.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9043   -1.8372   -2.8428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3190   -0.4224   -1.8250 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0999    0.9152   -2.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7645   -1.2303   -2.1617 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7870   -1.0232   -1.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8158   -1.6919   -1.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3575    0.1444   -0.3854 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9922    0.2117    0.9093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225   -0.3545    1.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2618    0.9039    1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3895    0.2809    0.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7216    0.9813    0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7997    0.2774   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9333   -1.1763    0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -0.3174   -0.2995 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0320    0.6467    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3849   -1.3826    2.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9223    0.2573    3.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0487    0.0019    1.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1758   -0.8771    0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6096    0.4507    2.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818    0.7388    1.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4236    0.6530   -1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3599   -1.0327   -2.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8925    0.9807   -2.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8348    0.9399   -3.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3335    1.7837   -1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785    1.0400   -1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1717    2.0173    0.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4865    0.9247    2.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5049   -0.7599    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2513    0.4589   -0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0137    0.8609    1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7206    2.0309    0.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7725    0.7889    0.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6551    0.3955   -1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0544   -1.7053   -0.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9216   -1.3928    1.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8767   -1.5355   -0.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1608   -1.3064    0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8896    1.6905    0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9564    0.5602    1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17 25  1  0
 25 26  1  0
 26  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  4  5  2  0
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 12 25  1  0
  5  6  1  0
 24 47  1  0
 24 48  1  0
 24 49  1  0
 23 45  1  0
 23 46  1  0
 22 43  1  0
 22 44  1  0
 21 41  1  0
 21 42  1  0
 20 39  1  0
 20 40  1  0
 17 38  1  6
 25 50  1  1
 26 51  1  0
 26 52  1  0
  8 33  1  0
  8 34  1  0
  3 31  1  0
  2 30  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 32  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
M  END


  Mrv1652304282218522D          

 26 28  0  0  1  0            999 V2000
   -1.2950   -0.0168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430   -0.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3190    0.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0401    0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0219    1.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5302    2.3371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288    1.8955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3809    1.2824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1259    0.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1345    1.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0483    2.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6614    2.9905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2413    2.6100    0.0000 O   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
    2.8490    0.3805    0.0000 O   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
    0.3439    2.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979   -1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049   -1.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0598   -2.3706    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  9 15  1  0  0  0  0
 12 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 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
  9 23  1  1  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0071507

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=O)[C@@H]1[C@H]2CC3=C(COC(\C=C\C)=C3)C(=O)[C@]2(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O5/c1-4-6-7-9-17(22)18-16-11-13-10-14(8-5-2)25-12-15(13)19(23)21(16,3)26-20(18)24/h5,8,10,16,18H,4,6-7,9,11-12H2,1-3H3/b8-5+/t16-,18+,21-/m1/s1

> <INCHI_KEY>
XXKNHBAFFJINCK-RVEJDSBJSA-N

> <FORMULA>
C21H26O5

> <MOLECULAR_WEIGHT>
358.434

> <EXACT_MASS>
358.178023937

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
40.31872870244646

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aR,9aR)-3-hexanoyl-9a-methyl-6-[(1E)-prop-1-en-1-yl]-2H,3H,3aH,4H,8H,9H,9aH-furo[3,2-g]isochromene-2,9-dione

> <ALOGPS_LOGP>
3.45

> <JCHEM_LOGP>
3.673164322666666

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.973419295848332

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8185930240977655

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
100.49789999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,9aR)-3-hexanoyl-9a-methyl-6-[(1E)-prop-1-en-1-yl]-3H,3aH,4H,8H-furo[3,2-g]isochromene-2,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0      -2.417  -0.031   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.387  -1.176   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.119  -0.856   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.595   0.609   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.435   1.754   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.941   1.433   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.041   3.218   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.990   4.363   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.547   3.538   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.578   2.394   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.102   0.929   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.984   3.020   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.823   4.552   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.968   5.582   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.317   4.872   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.318   2.250   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.318   0.710   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.652   3.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.986   2.250   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.319   3.020   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.653   2.250   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.987   3.020   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.642   4.784   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.863  -2.640   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.369  -2.961   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.845  -4.425   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15   23                                             
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9                                                       
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23    9                                                            
CONECT   24    2   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
Monascusone b	ChEBI

Chemical Formula

C₂₁H₂₆O₅

Average Mass

358.4340 Da

Monoisotopic Mass

358.17802 Da

IUPAC Name

(3S,3aR,9aR)-3-hexanoyl-9a-methyl-6-[(1E)-prop-1-en-1-yl]-2H,3H,3aH,4H,8H,9H,9aH-furo[3,2-g]isochromene-2,9-dione

Traditional Name

(3S,3aR,9aR)-3-hexanoyl-9a-methyl-6-[(1E)-prop-1-en-1-yl]-3H,3aH,4H,8H-furo[3,2-g]isochromene-2,9-dione

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)[C@@H]1[C@H]2CC3=C(COC(\C=C\C)=C3)C(=O)[C@]2(C)OC1=O

InChI Identifier

InChI=1S/C21H26O5/c1-4-6-7-9-17(22)18-16-11-13-10-14(8-5-2)25-12-15(13)19(23)21(16,3)26-20(18)24/h5,8,10,16,18H,4,6-7,9,11-12H2,1-3H3/b8-5+/t16-,18+,21-/m1/s1

InChI Key

XXKNHBAFFJINCK-RVEJDSBJSA-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 kaoliang	Fungi	KNApSAcK
Monascus pilosus	Fungi	KNApSAcK
Monascus purpureus Mentii	Fungi	KNApSAcK
Monascus spp.	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Alpha-acyloxy ketone
1,3-dicarbonyl compound
Pyran
Gamma butyrolactone
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:82621 )
polyketide (CHEBI:82621 )
gamma-lactone (CHEBI:82621 )
alpha,beta-unsaturated ketone (CHEBI:82621 )

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	3.45	ALOGPS
logP	3.67	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	10.97	ChemAxon
pKa (Strongest Basic)	-4.8	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	6	ChemAxon
Refractivity	100.5 m³·mol⁻¹	ChemAxon
Polarizability	40.32 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

C00030788

Chemspider ID

25043813

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12118082

PDB ID

Not Available

ChEBI ID

82621

Good Scents ID

Not Available

References

General References

Wu L, Zhou K, Chen F, Chen G, Yu Y, Lv X, Zhang W, Rao P, Ni L: Comparative Study on the Antioxidant Activity of Monascus Yellow Pigments From Two Different Types of Hongqu-Functional Qu and Coloring Qu. Front Microbiol. 2021 Aug 2;12:715295. doi: 10.3389/fmicb.2021.715295. eCollection 2021. [PubMed:34408740 ]
Adin SN, Gupta I, Panda BP, Mujeeb M: Monascin and ankaflavin-Biosynthesis from Monascus purpureus, production methods, pharmacological properties: A review. Biotechnol Appl Biochem. 2022 Mar 30. doi: 10.1002/bab.2336. [PubMed:35353924 ]
Lin CW, Chen HL, Yang YH, Chen YY, Hsu YW, Pan TM: Toxicological evaluation of the red mold rice extract, ANKASCIN 568-R: 13-week chronic toxicity, and genotoxicity studies. Toxicol Rep. 2022 Feb 22;9:356-365. doi: 10.1016/j.toxrep.2022.02.008. eCollection 2022. [PubMed:35284245 ]
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 ]
Lai JR, Hsu YW, Pan TM, Lee CL: Monascin and Ankaflavin of Monascus purpureus Prevent Alcoholic Liver Disease through Regulating AMPK-Mediated Lipid Metabolism and Enhancing Both Anti-Inflammatory and Anti-Oxidative Systems. Molecules. 2021 Oct 18;26(20). pii: molecules26206301. doi: 10.3390/molecules26206301. [PubMed:34684882 ]
Shaaban M, Magdy El-Metwally M, Mekawey AAI, Abdelwahab AB, Soltan MM: Monascin and monascinol, azaphilonoid pigments from Mortierella polycephala AM1: in silico and in vitro targeting of the angiogenic VEGFR2 kinase. Z Naturforsch C J Biosci. 2021 Jul 16;77(1-2):11-19. doi: 10.1515/znc-2021-0095. Print 2022 Jan 27. [PubMed:34265877 ]
Husakova M, Plechata M, Branska B, Patakova P: Effect of a Monascus sp. Red Yeast Rice Extract on Germination of Bacterial Spores. Front Microbiol. 2021 May 24;12:686100. doi: 10.3389/fmicb.2021.686100. eCollection 2021. [PubMed:34108955 ]
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 ]
Wu S, Sun Y, Chen D, Liu H, Li Z, Chen M, Wang C, Cheng L, Guo Q, Peng X: The noncovalent conjugations of human serum albumin (HSA) with MS/AK and the effect on anti-oxidant capacity as well as anti-glycation activity of Monascus yellow pigments. Food Funct. 2021 Apr 21;12(8):3692-3704. doi: 10.1039/d0fo03025b. Epub 2021 Apr 1. [PubMed:33900309 ]

Showing NP-Card for Monascin (NP0071507)

MOL for NP0071507 (Monascin)

3D MOL for NP0071507 (Monascin)

3D SDF for NP0071507 (Monascin)

3D-SDF for NP0071507 (Monascin)

PDB for NP0071507 (Monascin)

3D PDB for NP0071507 (Monascin)

SMILES for NP0071507 (Monascin)

INCHI for NP0071507 (Monascin)

Structure for NP0071507 (Monascin)

3D Structure for NP0071507 (Monascin)