NP-MRD: Showing NP-Card for BMY-28438 (NP0021139)

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Record Information

Version

2.0

Created at

2021-01-06 06:25:57 UTC

Updated at

2021-07-15 17:35:33 UTC

NP-MRD ID

NP0021139

Secondary Accession Numbers

None

Natural Product Identification

Common Name

BMY-28438

Provided By

NPAtlas

Description

3,7-Dihydroxytropolone is also known as bmy-28438. 3,7-Dihydroxytropolone 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. BMY-28438 is found in Streptomyces and Streptomyces cyaneofuscatus. BMY-28438 was first documented in 1988 (PMID: 3417559). Based on a literature review a small amount of articles have been published on 3,7-dihydroxytropolone (PMID: 16304149) (PMID: 29098212) (PMID: 2925523) (PMID: 29654178).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120413D          

 17 17  0  0  0  0            999 V2000
   -2.3778    1.8247   -0.4520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5789    0.9046   -0.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1096   -0.3796   -0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4110   -1.5507    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0527   -1.7740    0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581   -0.8123   -0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1548   -1.2756   -0.6156 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8852    0.5256    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0211    1.1438    0.6196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559    1.3207   -0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062    2.6619   -0.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1856   -0.4197   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0374   -2.4099    0.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3046   -2.7867    0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9120   -0.6429   -0.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8485    0.5945    0.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9182    3.0754    0.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10  2  1  0  0  0  0
  3 12  1  0  0  0  0
  4 13  1  0  0  0  0
  5 14  1  0  0  0  0
  7 15  1  0  0  0  0
  9 16  1  0  0  0  0
 11 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021139

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C([H])C(=O)C(O[H])=C1O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O4/c8-4-2-1-3-5(9)7(11)6(4)10/h1-3H,(H3,8,9,10,11)

> <INCHI_KEY>
HQLHJCFATKAUSO-UHFFFAOYSA-N

> <FORMULA>
C7H6O4

> <MOLECULAR_WEIGHT>
154.121

> <EXACT_MASS>
154.026608673

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.67756951409281

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3,4-trihydroxycyclohepta-2,4,6-trien-1-one

> <ALOGPS_LOGP>
-0.46

> <JCHEM_LOGP>
0.28947010633333325

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.48625567557513

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.927548113302745

> <JCHEM_PKA_STRONGEST_BASIC>
2.956922233701547

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
41.9036

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3,4-trihydroxycyclohepta-2,4,6-trien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.378   1.825  -0.452  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.579   0.905  -0.172  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.110  -0.380  -0.062  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.411  -1.551   0.146  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.053  -1.774   0.050  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.958  -0.812  -0.120  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.155  -1.276  -0.616  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.885   0.526   0.150  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.021   1.144   0.620  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.256   1.321  -0.011  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.006   2.662  -0.002  0.00  0.00           O+0
HETATM   12  H   UNK     0      -3.186  -0.420  -0.156  0.00  0.00           H+0
HETATM   13  H   UNK     0      -2.037  -2.410   0.426  0.00  0.00           H+0
HETATM   14  H   UNK     0       0.305  -2.787   0.107  0.00  0.00           H+0
HETATM   15  H   UNK     0       2.912  -0.643  -0.776  0.00  0.00           H+0
HETATM   16  H   UNK     0       2.849   0.595   0.760  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.918   3.075   0.107  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   15                                                       
CONECT    8    6    9   10                                                  
CONECT    9    8   16                                                       
CONECT   10    8   11    2                                                  
CONECT   11   10   17                                                       
CONECT   12    3                                                            
CONECT   13    4                                                            
CONECT   14    5                                                            
CONECT   15    7                                                            
CONECT   16    9                                                            
CONECT   17   11                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2,3,7-Trihydroxy-2,4,6-cycloheptatrien-1-one	ChEBI
BMY-28438	ChEBI

Chemical Formula

C₇H₆O₄

Average Mass

154.1210 Da

Monoisotopic Mass

154.02661 Da

IUPAC Name

2,3,4-trihydroxycyclohepta-2,4,6-trien-1-one

Traditional Name

2,3,4-trihydroxycyclohepta-2,4,6-trien-1-one

CAS Registry Number

Not Available

SMILES

OC1=CC=CC(=O)C(O)=C1O

InChI Identifier

InChI=1S/C7H6O4/c8-4-2-1-3-5(9)7(11)6(4)10/h1-3H,(H3,8,9,10,11)

InChI Key

HQLHJCFATKAUSO-UHFFFAOYSA-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
Streptomyces	NPAtlas	3417559
Streptomyces cyaneofuscatus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Streptomyces tropolofaciens No. K611-97	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	-0.46	ALOGPS
logP	0.29	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	7.93	ChemAxon
pKa (Strongest Basic)	2.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.9 m³·mol⁻¹	ChemAxon
Polarizability	13.68 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA020783

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00017929

Chemspider ID

114010

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

128646

PDB ID

Not Available

ChEBI ID

156362

Good Scents ID

Not Available

References

General References

Sugawara K, Ohbayashi M, Shimizu K, Hatori M, Kamei H, Konishi M, Oki T, Kawaguchi H: BMY-28438 (3,7-dihydroxytropolone), a new antitumor antibiotic active against B16 melanoma. I. Production, isolation, structure and biological activity. J Antibiot (Tokyo). 1988 Jul;41(7):862-8. doi: 10.7164/antibiotics.41.862. [PubMed:3417559 ]
Didierjean J, Isel C, Querre F, Mouscadet JF, Aubertin AM, Valnot JY, Piettre SR, Marquet R: Inhibition of human immunodeficiency virus type 1 reverse transcriptase, RNase H, and integrase activities by hydroxytropolones. Antimicrob Agents Chemother. 2005 Dec;49(12):4884-94. doi: 10.1128/AAC.49.12.4884-4894.2005. [PubMed:16304149 ]
Hirsch DR, Schiavone DV, Berkowitz AJ, Morrison LA, Masaoka T, Wilson JA, Lomonosova E, Zhao H, Patel BS, Datla SH, Hoft SG, Majidi SJ, Pal RK, Gallicchio E, Tang L, Tavis JE, Le Grice SFJ, Beutler JA, Murelli RP: Synthesis and biological assessment of 3,7-dihydroxytropolones. Org Biomol Chem. 2017 Dec 19;16(1):62-69. doi: 10.1039/c7ob02453c. [PubMed:29098212 ]
Tomita K, Hoshino Y, Nakakita Y, Umezawa S, Miyaki T, Oki T, Kawaguchi H: BMY-28438 (3,7-dihydroxytropolone), a new antitumor antibiotic active against B16 melanoma. II. Taxonomy of producing organism. J Antibiot (Tokyo). 1989 Feb;42(2):317-21. doi: 10.7164/antibiotics.42.317. [PubMed:2925523 ]
Chen X, Xu M, Lu J, Xu J, Wang Y, Lin S, Deng Z, Tao M: Biosynthesis of Tropolones in Streptomyces spp.: Interweaving Biosynthesis and Degradation of Phenylacetic Acid and Hydroxylations on the Tropone Ring. Appl Environ Microbiol. 2018 May 31;84(12). pii: AEM.00349-18. doi: 10.1128/AEM.00349-18. Print 2018 Jun 15. [PubMed:29654178 ]

Showing NP-Card for BMY-28438 (NP0021139)

MOL for NP0021139 (BMY-28438)

3D MOL for NP0021139 (BMY-28438)

3D SDF for NP0021139 (BMY-28438)

3D-SDF for NP0021139 (BMY-28438)

PDB for NP0021139 (BMY-28438)

3D PDB for NP0021139 (BMY-28438)

SMILES for NP0021139 (BMY-28438)

INCHI for NP0021139 (BMY-28438)

Structure for NP0021139 (BMY-28438)

3D Structure for NP0021139 (BMY-28438)