MiMeDB: Showing metabocard for Marinone (MMDBc0006392)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 23:37:26 UTC

Update Date

2022-08-31 06:25:16 UTC

Metabolite ID

MMDBc0006392

Metabolite Identification

Common Name

Marinone

Description

Marinone belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Marinone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152101372D          

 33 36  0  0  1  0            999 V2000
   -0.9403    4.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066    2.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9690   -2.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7035    0.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6225    1.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6354    2.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2391   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9690   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9017    1.5590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8889   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1618   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9274    3.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188   -0.6691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1589   -0.0454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6217   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8918   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8116   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7314   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2715    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4614    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8889    0.7341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8116   -2.3841    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.8918    0.7341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319   -2.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4614   -1.9164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415    1.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0787    0.8900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488    0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990    0.5782    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  6  2  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  2  0  0  0  0
 17 11  1  0  0  0  0
 18 14  1  0  0  0  0
 19 16  1  0  0  0  0
 20 19  2  0  0  0  0
 21 17  2  0  0  0  0
 21 20  1  0  0  0  0
 22 18  1  0  0  0  0
 22 20  1  0  0  0  0
 23 19  1  0  0  0  0
 24 18  2  0  0  0  0
 24 23  1  0  0  0  0
 25  4  1  1  0  0  0
 25  9  1  6  0  0  0
 25 15  1  0  0  0  0
 26 21  1  0  0  0  0
 27 16  1  0  0  0  0
 28 17  1  0  0  0  0
 29 22  2  0  0  0  0
 30 23  2  0  0  0  0
 31 24  1  0  0  0  0
 31 25  1  0  0  0  0
 14 32  1  6  0  0  0
 15 33  1  6  0  0  0
M  END


  Mrv1652305152101372D          

 33 36  0  0  1  0            999 V2000
   -0.9403    4.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066    2.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9690   -2.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7035    0.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6225    1.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6354    2.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2391   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9690   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9017    1.5590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8889   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1618   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9274    3.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188   -0.6691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1589   -0.0454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6217   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8918   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8116   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7314   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2715    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4614    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8889    0.7341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8116   -2.3841    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.8918    0.7341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319   -2.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4614   -1.9164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415    1.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0787    0.8900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488    0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990    0.5782    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  6  2  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  2  0  0  0  0
 17 11  1  0  0  0  0
 18 14  1  0  0  0  0
 19 16  1  0  0  0  0
 20 19  2  0  0  0  0
 21 17  2  0  0  0  0
 21 20  1  0  0  0  0
 22 18  1  0  0  0  0
 22 20  1  0  0  0  0
 23 19  1  0  0  0  0
 24 18  2  0  0  0  0
 24 23  1  0  0  0  0
 25  4  1  1  0  0  0
 25  9  1  6  0  0  0
 25 15  1  0  0  0  0
 26 21  1  0  0  0  0
 27 16  1  0  0  0  0
 28 17  1  0  0  0  0
 29 22  2  0  0  0  0
 30 23  2  0  0  0  0
 31 24  1  0  0  0  0
 31 25  1  0  0  0  0
 14 32  1  6  0  0  0
 15 33  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0006392

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CCC(C)=C[C@]1([H])C1=C(O[C@@]2(C)CCC=C(C)C)C(=O)C2=C(C(Br)=C(O)C=C2O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H27BrO5/c1-12(2)6-5-9-25(4)15-8-7-13(3)10-14(15)18-22(29)20-19(23(30)24(18)31-25)16(27)11-17(28)21(20)26/h6,10-11,14-15,27-28H,5,7-9H2,1-4H3/t14-,15+,25-/m0/s1

> <INCHI_KEY>
DONXAKUQFKTOAJ-AYNSBQOLSA-N

> <FORMULA>
C25H27BrO5

> <MOLECULAR_WEIGHT>
487.39

> <EXACT_MASS>
486.104187

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
48.522195706795074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aR,5S,12bS)-11-bromo-8,10-dihydroxy-2,5-dimethyl-5-(4-methylpent-3-en-1-yl)-4,4a,5,7,12,12b-hexahydro-3H-6-oxatetraphene-7,12-dione

> <ALOGPS_LOGP>
5.01

> <JCHEM_LOGP>
5.660358575

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.34983696941606

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.972173365993343

> <JCHEM_PKA_STRONGEST_BASIC>
-5.004424146620062

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
126.31409999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,5S,12bS)-11-bromo-8,10-dihydroxy-2,5-dimethyl-5-(4-methylpent-3-en-1-yl)-3,4,4a,12b-tetrahydro-6-oxatetraphene-7,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -1.755   7.530   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.386   5.241   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.676  -4.450   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.180   1.614   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.029   3.659   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.053   5.199   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.180  -1.831   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.676  -0.376   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.683   2.910   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.659  -2.704   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.902  -1.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.731   5.990   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.171  -2.995   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.155  -1.249   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.163  -0.085   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.894  -0.085   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.398  -2.704   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.357  -0.958   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.382  -0.376   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.878  -1.831   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.886  -2.995   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.365  -2.122   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.373   0.788   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.861   0.497   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.659   1.370   0.000  0.00  0.00           C+0
HETATM   26 Br   UNK     0       3.382  -4.450   0.000  0.00  0.00          Br+0
HETATM   27  O   UNK     0       5.398   1.370   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.406  -3.868   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.861  -3.577   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.878   2.243   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.147   1.661   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0      -0.651   0.206   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.171   1.079   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   25                                                            
CONECT    5    6    9                                                       
CONECT    6    5   12                                                       
CONECT    7    8   13                                                       
CONECT    8    7   15                                                       
CONECT    9    5   25                                                       
CONECT   10   13   14                                                       
CONECT   11   16   17                                                       
CONECT   12    1    2    6                                                  
CONECT   13    3    7   10                                                  
CONECT   14   10   15   18   32                                             
CONECT   15    8   14   25   33                                             
CONECT   16   11   19   27                                                  
CONECT   17   11   21   28                                                  
CONECT   18   14   22   24                                                  
CONECT   19   16   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   17   20   26                                                  
CONECT   22   18   20   29                                                  
CONECT   23   19   24   30                                                  
CONECT   24   18   23   31                                                  
CONECT   25    4    9   15   31                                             
CONECT   26   21                                                            
CONECT   27   16                                                            
CONECT   28   17                                                            
CONECT   29   22                                                            
CONECT   30   23                                                            
CONECT   31   24   25                                                       
CONECT   32   14                                                            
CONECT   33   15                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

Synonyms

Not Available

Molecular Formula

C₂₅H₂₇BrO₅

Average Mass

487.39

Monoisotopic Mass

486.104187

IUPAC Name

(4aR,5S,12bS)-11-bromo-8,10-dihydroxy-2,5-dimethyl-5-(4-methylpent-3-en-1-yl)-4,4a,5,7,12,12b-hexahydro-3H-6-oxatetraphene-7,12-dione

Traditional Name

(4aR,5S,12bS)-11-bromo-8,10-dihydroxy-2,5-dimethyl-5-(4-methylpent-3-en-1-yl)-3,4,4a,12b-tetrahydro-6-oxatetraphene-7,12-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(C)=C[C@]1([H])C1=C(O[C@@]2(C)CCC=C(C)C)C(=O)C2=C(C(Br)=C(O)C=C2O)C1=O

InChI Identifier

InChI=1S/C25H27BrO5/c1-12(2)6-5-9-25(4)15-8-7-13(3)10-14(15)18-22(29)20-19(23(30)24(18)31-25)16(27)11-17(28)21(20)26/h6,10-11,14-15,27-28H,5,7-9H2,1-4H3/t14-,15+,25-/m0/s1

InChI Key

DONXAKUQFKTOAJ-AYNSBQOLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Naphthoquinone
Naphthalene
4-halophenol
2-halophenol
2-bromophenol
4-bromophenol
Quinone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Aryl halide
Aryl bromide
Pyran
Benzenoid
Vinylogous acid
Vinylogous ester
Vinylogous halide
Ketone
Oxacycle
Organooxygen compound
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.009 g/L	ALOGPS
logP	5.01	ALOGPS
logP	5.66	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	5.97	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	126.31 m³·mol⁻¹	ChemAxon
Polarizability	48.52 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	2	Human	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8633563

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Marinone

METLIN ID

Not Available

PubChem Compound

10458149

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Marinone (MMDBc0006392)

MOL for #<Metabolite:0x00007fecdb94f8e8>

3D MOL for #<Metabolite:0x00007fecdb94f8e8>

3D SDF for #<Metabolite:0x00007fecdb94f8e8>

3D-SDF for #<Metabolite:0x00007fecdb94f8e8>

PDB for #<Metabolite:0x00007fecdb94f8e8>

3D PDB for #<Metabolite:0x00007fecdb94f8e8>

SMILES for #<Metabolite:0x00007fecdb94f8e8>

INCHI for #<Metabolite:0x00007fecdb94f8e8>

Structure for #<Metabolite:0x00007fecdb94f8e8>

3D Structure for #<Metabolite:0x00007fecdb94f8e8>