MiMeDB: Showing metabocard for Shamixanthone (MMDBc0014271)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 05:21:06 UTC

Update Date

2022-08-31 06:37:27 UTC

Metabolite ID

MMDBc0014271

Metabolite Identification

Common Name

Shamixanthone

Description

(3R,4S)-4,6-dihydroxy-12-methyl-9-(3-methylbut-2-en-1-yl)-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-5-one belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group (3R,4S)-4,6-dihydroxy-12-methyl-9-(3-methylbut-2-en-1-yl)-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-5-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152107212D          

 32 35  0  0  1  0            999 V2000
   -1.2715    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913    1.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2096    3.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5598    3.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2096   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787   -0.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8593   -0.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0197    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4614    0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497    3.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4796    2.4296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6990    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193    0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5893    1.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3994    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695    2.2736    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0492    1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690    3.2091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294    2.8973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193    2.7414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497    1.0264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091    0.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395    3.0532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8593    2.1177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  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  2  0  0  0  0
 13  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14 10  2  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  1  6  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 17  2  0  0  0  0
 20 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22 16  1  0  0  0  0
 22 21  1  0  0  0  0
 23 19  1  0  0  0  0
 23 20  1  0  0  0  0
 24 14  1  0  0  0  0
 24 21  2  0  0  0  0
 25 15  2  0  0  0  0
 25 19  1  0  0  0  0
 26 17  1  0  0  0  0
 22 27  1  1  0  0  0
 28 23  2  0  0  0  0
 29 11  1  0  0  0  0
 29 24  1  0  0  0  0
 30 18  1  0  0  0  0
 30 25  1  0  0  0  0
 16 31  1  1  0  0  0
 22 32  1  6  0  0  0
M  END


  Mrv1652305152107212D          

 32 35  0  0  1  0            999 V2000
   -1.2715    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913    1.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2096    3.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5598    3.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2096   -0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787   -0.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8593   -0.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0197    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4614    0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497    3.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4796    2.4296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6990    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193    0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5893    1.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3994    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695    2.2736    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0492    1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690    3.2091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294    2.8973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193    2.7414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497    1.0264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091    0.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395    3.0532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8593    2.1177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  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  2  0  0  0  0
 13  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14 10  2  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  1  6  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 17  2  0  0  0  0
 20 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22 16  1  0  0  0  0
 22 21  1  0  0  0  0
 23 19  1  0  0  0  0
 23 20  1  0  0  0  0
 24 14  1  0  0  0  0
 24 21  2  0  0  0  0
 25 15  2  0  0  0  0
 25 19  1  0  0  0  0
 26 17  1  0  0  0  0
 22 27  1  1  0  0  0
 28 23  2  0  0  0  0
 29 11  1  0  0  0  0
 29 24  1  0  0  0  0
 30 18  1  0  0  0  0
 30 25  1  0  0  0  0
 16 31  1  1  0  0  0
 22 32  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0014271

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(O)C2=C(OC[C@@]1([H])C(C)=C)C(C)=CC1=C2C(=O)C2=C(O)C=CC(CC=C(C)C)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O5/c1-12(2)6-7-15-8-9-17(26)19-23(28)20-18(30-25(15)19)10-14(5)24-21(20)22(27)16(11-29-24)13(3)4/h6,8-10,16,22,26-27H,3,7,11H2,1-2,4-5H3/t16-,22-/m0/s1

> <INCHI_KEY>
MXGMZMKTWCNKRS-AOMKIAJQSA-N

> <FORMULA>
C25H26O5

> <MOLECULAR_WEIGHT>
406.478

> <EXACT_MASS>
406.178023937

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
45.12377772598683

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4S)-4,6-dihydroxy-12-methyl-9-(3-methylbut-2-en-1-yl)-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-5-one

> <ALOGPS_LOGP>
3.76

> <JCHEM_LOGP>
5.4345096296666675

> <ALOGPS_LOGS>
-4.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.608365452593102

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.377191148645602

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4091993111862084

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
117.27039999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.68e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
shamixanthone

> <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      -2.373   0.752   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.357   2.498   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.725   7.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.245   6.281   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.725  -0.994   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.147  -0.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.659   0.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.155   2.789   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.659   4.244   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.204  -0.121   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.237   3.371   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.861   1.043   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.733   5.990   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.716   0.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.163   1.625   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.229   4.535   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.171   4.535   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.196   1.043   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.180   3.371   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.700   2.498   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.212   2.789   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.716   4.244   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.692   3.662   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.220   1.625   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.676   1.916   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.676   5.990   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       7.708   5.408   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.196   5.117   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      10.733   1.916   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.684   0.752   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0       9.220   5.699   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       7.204   3.953   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5   14                                                            
CONECT    6    7   12                                                       
CONECT    7    6   15                                                       
CONECT    8    9   15                                                       
CONECT    9    8   17                                                       
CONECT   10   14   18                                                       
CONECT   11   16   29                                                       
CONECT   12    1    2    6                                                  
CONECT   13    3    4   16                                                  
CONECT   14    5   10   24                                                  
CONECT   15    7    8   25                                                  
CONECT   16   11   13   22   31                                             
CONECT   17    9   19   26                                                  
CONECT   18   10   20   30                                                  
CONECT   19   17   23   25                                                  
CONECT   20   18   21   23                                                  
CONECT   21   20   22   24                                                  
CONECT   22   16   21   27   32                                             
CONECT   23   19   20   28                                                  
CONECT   24   14   21   29                                                  
CONECT   25   15   19   30                                                  
CONECT   26   17                                                            
CONECT   27   22                                                            
CONECT   28   23                                                            
CONECT   29   11   24                                                       
CONECT   30   18   25                                                       
CONECT   31   16                                                            
CONECT   32   22                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

Synonyms

Not Available

Molecular Formula

C₂₅H₂₆O₅

Average Mass

406.478

Monoisotopic Mass

406.178023937

IUPAC Name

(3R,4S)-4,6-dihydroxy-12-methyl-9-(3-methylbut-2-en-1-yl)-3-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1,10-dioxatetraphen-5-one

Traditional Name

shamixanthone

CAS Registry Number

Not Available

SMILES

[H][C@@]1(O)C2=C(OC[C@@]1([H])C(C)=C)C(C)=CC1=C2C(=O)C2=C(O)C=CC(CC=C(C)C)=C2O1

InChI Identifier

InChI=1S/C25H26O5/c1-12(2)6-7-15-8-9-17(26)19-23(28)20-18(30-25(15)19)10-14(5)24-21(20)22(27)16(11-29-24)13(3)4/h6,8-10,16,22,26-27H,3,7,11H2,1-2,4-5H3/t16-,22-/m0/s1

InChI Key

MXGMZMKTWCNKRS-AOMKIAJQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

4-prenylated xanthones

Alternative Parents

Substituents

4-prenylated xanthone
Pyranoxanthone
Chromone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Ether
Oxacycle
Organooxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
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	0.0097 g/L	ALOGPS
logP	3.76	ALOGPS
logP	5.43	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.38	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	117.27 m³·mol⁻¹	ChemAxon
Polarizability	45.12 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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
Eukaryota/Fungi	Ascomycota	2	Human feces	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

10479697

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12112141

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 Shamixanthone (MMDBc0014271)

MOL for #<Metabolite:0x00007fecc5674080>

3D MOL for #<Metabolite:0x00007fecc5674080>

3D SDF for #<Metabolite:0x00007fecc5674080>

3D-SDF for #<Metabolite:0x00007fecc5674080>

PDB for #<Metabolite:0x00007fecc5674080>

3D PDB for #<Metabolite:0x00007fecc5674080>

SMILES for #<Metabolite:0x00007fecc5674080>

INCHI for #<Metabolite:0x00007fecc5674080>

Structure for #<Metabolite:0x00007fecc5674080>

3D Structure for #<Metabolite:0x00007fecc5674080>