MiMeDB: Showing metabocard for Kiamycin B (MMDBc0024001)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 13:52:39 UTC

Update Date

2022-08-31 06:48:59 UTC

Metabolite ID

MMDBc0024001

Metabolite Identification

Common Name

Kiamycin B

Description

Kiamycin B belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. Kiamycin B is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152115522D          

 30 34  0  0  1  0            999 V2000
   -0.6613   -1.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6895   -3.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4367   -1.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8801   -1.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1876   -2.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4983   -0.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -1.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415   -2.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1662   -1.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0745   -1.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3590   -2.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3820   -2.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3271   -0.2319    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6713   -1.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8254   -1.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5332   -1.5106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3602   -0.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9555   -2.0219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0364   -1.9090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6988   -1.0524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8640   -3.1024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4700   -2.6889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5183   -2.5197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1649   -0.3717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1329   -3.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011    0.0102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1848    0.5808    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2584   -2.2885    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -0.2564    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3493   -2.7469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 11  8  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14  9  2  0  0  0  0
 14 11  1  0  0  0  0
 15 10  2  0  0  0  0
 15 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  1  0  0  0
 19  7  1  0  0  0  0
 19  8  1  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 20 18  1  0  0  0  0
 21 11  2  0  0  0  0
 18 22  1  1  0  0  0
 19 23  1  6  0  0  0
 20 24  1  1  0  0  0
 25  2  1  0  0  0  0
 25 12  1  0  0  0  0
 26 13  1  0  0  0  0
 26 17  1  0  0  0  0
 13 27  1  1  0  0  0
 16 28  1  1  0  0  0
 17 29  1  6  0  0  0
 18 30  1  6  0  0  0
M  END


  Mrv1652305152115522D          

 30 34  0  0  1  0            999 V2000
   -0.6613   -1.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6895   -3.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4367   -1.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8801   -1.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1876   -2.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4983   -0.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -1.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415   -2.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1662   -1.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0745   -1.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3590   -2.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3820   -2.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3271   -0.2319    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6713   -1.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8254   -1.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5332   -1.5106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3602   -0.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9555   -2.0219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0364   -1.9090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6988   -1.0524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8640   -3.1024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4700   -2.6889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5183   -2.5197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1649   -0.3717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1329   -3.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011    0.0102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1848    0.5808    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2584   -2.2885    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -0.2564    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3493   -2.7469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 11  8  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14  9  2  0  0  0  0
 14 11  1  0  0  0  0
 15 10  2  0  0  0  0
 15 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  1  0  0  0
 19  7  1  0  0  0  0
 19  8  1  0  0  0  0
 20 13  1  0  0  0  0
 20 16  1  0  0  0  0
 20 18  1  0  0  0  0
 21 11  2  0  0  0  0
 18 22  1  1  0  0  0
 19 23  1  6  0  0  0
 20 24  1  1  0  0  0
 25  2  1  0  0  0  0
 25 12  1  0  0  0  0
 26 13  1  0  0  0  0
 26 17  1  0  0  0  0
 13 27  1  1  0  0  0
 16 28  1  1  0  0  0
 17 29  1  6  0  0  0
 18 30  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0024001

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CC3=C(C(=O)C[C@](C)(O)C3)[C@@]3([H])[C@@]([H])(O1)C1=C(C(OC)=CC=C1)[C@@]([H])(O)[C@@]23O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O6/c1-19(23)7-9-6-13-20(24)16(14(9)11(21)8-19)17(26-13)10-4-3-5-12(25-2)15(10)18(20)22/h3-5,13,16-18,22-24H,6-8H2,1-2H3/t13-,16-,17-,18+,19+,20+/m0/s1

> <INCHI_KEY>
OYXKPETZJCTWDM-GYDQMFFNSA-N

> <FORMULA>
C20H22O6

> <MOLECULAR_WEIGHT>
358.39

> <EXACT_MASS>
358.141638428

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.108827929310735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,9S,11R,18R,19R)-5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0^{2,7}.0^{9,19}.0^{12,17}]nonadeca-2(7),12(17),13,15-tetraen-3-one

> <ALOGPS_LOGP>
-0.18

> <JCHEM_LOGP>
-0.05873108633333274

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.777357117751546

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.284136566747655

> <JCHEM_PKA_STRONGEST_BASIC>
-2.890971617659144

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
92.5084

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,9S,11R,18R,19R)-5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0^{2,7}.0^{9,19}.0^{12,17}]nonadeca-2(7),12(17),13,15-tetraen-3-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      -1.234  -2.742   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.754  -7.429   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.149  -3.024   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.110  -1.888   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.684  -4.493   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.797  -0.500   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.651  -2.138   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.011  -4.781   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.177  -1.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.606  -2.219   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.537  -4.573   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.180  -4.824   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.344  -0.433   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.120  -3.148   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.141  -3.687   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.729  -2.820   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.272  -1.450   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.517  -3.774   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.068  -3.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.038  -1.964   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.480  -5.791   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.611  -5.019   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.967  -4.703   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.908  -0.694   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.715  -6.292   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.789   0.019   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       4.078   1.084   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.216  -4.272   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       7.467  -0.479   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       6.252  -5.127   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2   25                                                            
CONECT    3    4    5                                                       
CONECT    4    3   10                                                       
CONECT    5    3   12                                                       
CONECT    6    9   13                                                       
CONECT    7    9   19                                                       
CONECT    8   11   19                                                       
CONECT    9    6    7   14                                                  
CONECT   10    4   15   17                                                  
CONECT   11    8   14   21                                                  
CONECT   12    5   15   25                                                  
CONECT   13    6   20   26   27                                             
CONECT   14    9   11   16                                                  
CONECT   15   10   12   18                                                  
CONECT   16   14   17   20   28                                             
CONECT   17   10   16   26   29                                             
CONECT   18   15   20   22   30                                             
CONECT   19    1    7    8   23                                             
CONECT   20   13   16   18   24                                             
CONECT   21   11                                                            
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   20                                                            
CONECT   25    2   12                                                       
CONECT   26   13   17                                                       
CONECT   27   13                                                            
CONECT   28   16                                                            
CONECT   29   17                                                            
CONECT   30   18                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

Synonyms

Not Available

Molecular Formula

C₂₀H₂₂O₆

Average Mass

358.39

Monoisotopic Mass

358.141638428

IUPAC Name

(1S,5R,9S,11R,18R,19R)-5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0^{2,7}.0^{9,19}.0^{12,17}]nonadeca-2(7),12(17),13,15-tetraen-3-one

Traditional Name

(1S,5R,9S,11R,18R,19R)-5,18,19-trihydroxy-16-methoxy-5-methyl-10-oxapentacyclo[9.8.0.0^{2,7}.0^{9,19}.0^{12,17}]nonadeca-2(7),12(17),13,15-tetraen-3-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC3=C(C(=O)C[C@](C)(O)C3)[C@@]3([H])[C@@]([H])(O1)C1=C(C(OC)=CC=C1)[C@@]([H])(O)[C@@]23O

InChI Identifier

InChI=1S/C20H22O6/c1-19(23)7-9-6-13-20(24)16(14(9)11(21)8-19)17(26-13)10-4-3-5-12(25-2)15(10)18(20)22/h3-5,13,16-18,22-24H,6-8H2,1-2H3/t13-,16-,17-,18+,19+,20+/m0/s1

InChI Key

OYXKPETZJCTWDM-GYDQMFFNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Anisole
Cyclohexenone
Alkyl aryl ether
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.58 g/L	ALOGPS
logP	-0.18	ALOGPS
logP	-0.059	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.28	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.51 m³·mol⁻¹	ChemAxon
Polarizability	37.11 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
Bacteria	Actinobacteria	1		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

71048997

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139591250

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 Kiamycin B (MMDBc0024001)

MOL for #<Metabolite:0x00007fed152eb0f8>

3D MOL for #<Metabolite:0x00007fed152eb0f8>

3D SDF for #<Metabolite:0x00007fed152eb0f8>

3D-SDF for #<Metabolite:0x00007fed152eb0f8>

PDB for #<Metabolite:0x00007fed152eb0f8>

3D PDB for #<Metabolite:0x00007fed152eb0f8>

SMILES for #<Metabolite:0x00007fed152eb0f8>

INCHI for #<Metabolite:0x00007fed152eb0f8>

Structure for #<Metabolite:0x00007fed152eb0f8>

3D Structure for #<Metabolite:0x00007fed152eb0f8>