MiMeDB: Showing metabocard for Hericenone B (MMDBc0011623)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 03:25:48 UTC

Update Date

2022-12-15 22:51:44 UTC

Metabolite ID

MMDBc0011623

Metabolite Identification

Common Name

Hericenone B

Description

Hericenone B belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. Based on a literature review very few articles have been published on Hericenone B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152105252D          

 33 35  0  0  0  0            999 V2000
    9.0681   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.6979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 11 10  1  0  0  0  0
 13 12  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18 14  2  0  0  0  0
 19  3  1  0  0  0  0
 19 10  2  0  0  0  0
 19 15  1  0  0  0  0
 20  8  2  0  0  0  0
 20  9  1  0  0  0  0
 20 12  1  0  0  0  0
 21 16  2  0  0  0  0
 21 17  1  0  0  0  0
 22 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23 11  1  0  0  0  0
 24 16  1  0  0  0  0
 24 23  2  0  0  0  0
 25 21  1  0  0  0  0
 26 23  1  0  0  0  0
 26 25  2  0  0  0  0
 27 25  1  0  0  0  0
 28 13  1  0  0  0  0
 28 17  1  0  0  0  0
 28 27  1  0  0  0  0
 29 22  2  0  0  0  0
 30 26  1  0  0  0  0
 31 27  2  0  0  0  0
 32  4  1  0  0  0  0
 32 24  1  0  0  0  0
 33 10  1  0  0  0  0
M  END


  Mrv1652305152105252D          

 33 35  0  0  0  0            999 V2000
    9.0681   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.6979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 11 10  1  0  0  0  0
 13 12  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18 14  2  0  0  0  0
 19  3  1  0  0  0  0
 19 10  2  0  0  0  0
 19 15  1  0  0  0  0
 20  8  2  0  0  0  0
 20  9  1  0  0  0  0
 20 12  1  0  0  0  0
 21 16  2  0  0  0  0
 21 17  1  0  0  0  0
 22 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23 11  1  0  0  0  0
 24 16  1  0  0  0  0
 24 23  2  0  0  0  0
 25 21  1  0  0  0  0
 26 23  1  0  0  0  0
 26 25  2  0  0  0  0
 27 25  1  0  0  0  0
 28 13  1  0  0  0  0
 28 17  1  0  0  0  0
 28 27  1  0  0  0  0
 29 22  2  0  0  0  0
 30 26  1  0  0  0  0
 31 27  2  0  0  0  0
 32  4  1  0  0  0  0
 32 24  1  0  0  0  0
 33 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0011623

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(CC1=C(OC)C=C2CN(CCC3=CC=CC=C3)C(=O)C2=C1O)=C(C)CC(=O)C=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H31NO4/c1-18(2)14-22(29)15-19(3)10-11-23-24(32-4)16-21-17-28(27(31)25(21)26(23)30)13-12-20-8-6-5-7-9-20/h5-10,14,16,30H,11-13,15,17H2,1-4H3/b19-10+

> <INCHI_KEY>
ZJTHOPGQZOXEJX-VXLYETTFSA-N

> <FORMULA>
C27H31NO4

> <MOLECULAR_WEIGHT>
433.548

> <EXACT_MASS>
433.225308482

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
49.434043682473124

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-2,3-dihydro-1H-isoindol-1-one

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
5.793171973333335

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.597952422096235

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.804894585553494

> <JCHEM_PKA_STRONGEST_BASIC>
-1.641885330238242

> <JCHEM_POLAR_SURFACE_AREA>
66.84

> <JCHEM_REFRACTIVITY>
129.95959999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3H-isoindol-1-one

> <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      16.927  -2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.593  -4.383   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.710  -2.637   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.940  -3.970   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.940  -1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.400  -3.970   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.260  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.592  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.593  -2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.926  -2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       1.220  -1.303   0.000  0.00  0.00           N+0
HETATM   29  O   UNK     0      12.926  -4.383   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       7.591  -1.303   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   32                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   20                                                       
CONECT    9    7   20                                                       
CONECT   10   11   19   33                                                  
CONECT   11   10   23                                                       
CONECT   12   13   20                                                       
CONECT   13   12   28                                                       
CONECT   14   18   22                                                       
CONECT   15   19   22                                                       
CONECT   16   21   24                                                       
CONECT   17   21   28                                                       
CONECT   18    1    2   14                                                  
CONECT   19    3   10   15                                                  
CONECT   20    8    9   12                                                  
CONECT   21   16   17   25                                                  
CONECT   22   14   15   29                                                  
CONECT   23   11   24   26                                                  
CONECT   24   16   23   32                                                  
CONECT   25   21   26   27                                                  
CONECT   26   23   25   30                                                  
CONECT   27   25   28   31                                                  
CONECT   28   13   17   27                                                  
CONECT   29   22                                                            
CONECT   30   26                                                            
CONECT   31   27                                                            
CONECT   32    4   24                                                       
CONECT   33   10                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

Synonyms

Not Available

Molecular Formula

C₂₇H₃₁NO₄

Average Mass

433.548

Monoisotopic Mass

433.225308482

IUPAC Name

6-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-2,3-dihydro-1H-isoindol-1-one

Traditional Name

6-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3H-isoindol-1-one

CAS Registry Number

Not Available

SMILES

[H]C(CC1=C(OC)C=C2CN(CCC3=CC=CC=C3)C(=O)C2=C1O)=C(C)CC(=O)C=C(C)C

InChI Identifier

InChI=1S/C27H31NO4/c1-18(2)14-22(29)15-19(3)10-11-23-24(32-4)16-21-17-28(27(31)25(21)26(23)30)13-12-20-8-6-5-7-9-20/h5-10,14,16,30H,11-13,15,17H2,1-4H3/b19-10+

InChI Key

ZJTHOPGQZOXEJX-VXLYETTFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Aromatic monoterpenoid
Bicyclic monoterpenoid
Monoterpenoid
Isoindolone
Isoindole
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Vinylogous acid
Alpha,beta-unsaturated ketone
Tertiary carboxylic acid amide
Enone
Carboxamide group
Lactam
Ketone
Ether
Carboxylic acid derivative
Azacycle
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organic oxygen compound
Organopnictogen 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	0.0027 g/L	ALOGPS
logP	4.29	ALOGPS
logP	5.79	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.84 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	129.96 m³·mol⁻¹	ChemAxon
Polarizability	49.43 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Membrane

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
Eukaryota/Fungi	Basidiomycota	3	Human feces	Metabolic reconstruction

Exposure Sources

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

C00023976

Chemspider ID

78434889

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14482559

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 Hericenone B (MMDBc0011623)

MOL for #<Metabolite:0x00007fdb45c52268>

3D MOL for #<Metabolite:0x00007fdb45c52268>

3D SDF for #<Metabolite:0x00007fdb45c52268>

3D-SDF for #<Metabolite:0x00007fdb45c52268>

PDB for #<Metabolite:0x00007fdb45c52268>

3D PDB for #<Metabolite:0x00007fdb45c52268>

SMILES for #<Metabolite:0x00007fdb45c52268>

INCHI for #<Metabolite:0x00007fdb45c52268>

Structure for #<Metabolite:0x00007fdb45c52268>

3D Structure for #<Metabolite:0x00007fdb45c52268>