NP-MRD: Showing NP-Card for {5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate (NP0238299)

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Record Information

Version

2.0

Created at

2022-09-06 21:40:15 UTC

Updated at

2022-09-06 21:40:16 UTC

NP-MRD ID

NP0238299

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate

Description

{5-Methyl-4,9-dioxo-4H,9H-naphtho[2,3-b]furan-3-yl}methyl formate belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. It was first documented in 2022 (PMID: 36088123). Based on a literature review a significant number of articles have been published on {5-methyl-4,9-dioxo-4H,9H-naphtho[2,3-b]furan-3-yl}methyl formate (PMID: 36088122) (PMID: 36088121) (PMID: 36088120) (PMID: 36088119).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    2.0185   -1.9507    2.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4139   -0.8264    1.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7191   -0.4772    1.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1264    0.4252    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2074    0.9953   -0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8973    0.6358   -0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678   -0.2621    0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0633   -0.5497    0.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -1.3826    1.3542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105    0.1059   -0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2921    0.0777   -0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1219   -0.7760    0.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8074    0.1115    1.2411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6563    1.0968    1.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0913    1.4791   -0.0641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6780    0.9051   -1.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082    1.4688   -2.0216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5210    1.0185   -1.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8754    1.2915   -1.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2971    2.0912   -2.3847 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287   -2.7082    1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9279   -2.5866    2.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4874   -1.6915    2.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4949   -0.8731    1.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1582    0.7121    0.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5040    1.7272   -1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5096   -1.4786    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8916   -1.3672   -0.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0376    1.6601    1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6785    1.1283   -1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 18  2  0
 18 17  1  0
 17 16  1  0
 16 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 18 19  1  0
 19 20  2  0
  7  2  1  0
 11 10  1  0
 19  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
 16 30  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
M  END


  Mrv1652309062223402D          

 20 22  0  0  0  0            999 V2000
    4.0668   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    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
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    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
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   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
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -1.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 18  2  0  0  0  0
 18 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0238299

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC=CC2=C1C(=O)C1=C(OC=C1COC=O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c1-8-3-2-4-10-11(8)14(18)12-9(5-19-7-16)6-20-15(12)13(10)17/h2-4,6-7H,5H2,1H3

> <INCHI_KEY>
OIVPIPQHGVUCJC-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.24

> <EXACT_MASS>
270.052823422

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.46690186123231

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{5-methyl-4,9-dioxo-4H,9H-naphtho[2,3-b]furan-3-yl}methyl formate

> <JCHEM_LOGP>
2.117451043

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.15891825588031

> <JCHEM_POLAR_SURFACE_AREA>
73.58000000000001

> <JCHEM_REFRACTIVITY>
70.06

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
{5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       7.591  -0.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.680  -1.012   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.204  -2.477   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.235  -3.621   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   11   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   19                                                  
CONECT   19   18    6   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
{5-methyl-4,9-dioxo-4H,9H-naphtho[2,3-b]furan-3-yl}methyl formic acid	Generator

Chemical Formula

C₁₅H₁₀O₅

Average Mass

270.2400 Da

Monoisotopic Mass

270.05282 Da

IUPAC Name

{5-methyl-4,9-dioxo-4H,9H-naphtho[2,3-b]furan-3-yl}methyl formate

Traditional Name

{5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate

CAS Registry Number

Not Available

SMILES

CC1=CC=CC2=C1C(=O)C1=C(OC=C1COC=O)C2=O

InChI Identifier

InChI=1S/C15H10O5/c1-8-3-2-4-10-11(8)14(18)12-9(5-19-7-16)6-20-15(12)13(10)17/h2-4,6-7H,5H2,1H3

InChI Key

OIVPIPQHGVUCJC-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Naphthalene
Aryl ketone
Benzenoid
Furan
Heteroaromatic compound
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.12	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	73.58 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.06 m³·mol⁻¹	ChemAxon
Polarizability	26.47 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163192691

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xu X, Rothrock MJ Jr, Reeves J, Kumar GD, Mishra A: Using E. coli population to predict foodborne pathogens in pastured poultry farms. Food Microbiol. 2022 Dec;108:104092. doi: 10.1016/j.fm.2022.104092. Epub 2022 Jul 14. [PubMed:36088123 ]
Lanzl MI, Zwietering MH, Abee T, den Besten HMW: Combining enrichment with multiplex real-time PCR leads to faster detection and identification of Campylobacter spp. in food compared to ISO 10272-1:2017. Food Microbiol. 2022 Dec;108:104117. doi: 10.1016/j.fm.2022.104117. Epub 2022 Aug 19. [PubMed:36088122 ]
Cacciatore FA, Maders C, Alexandre B, Barreto Pinilla CM, Brandelli A, da Silva Malheiros P: Carvacrol encapsulation into nanoparticles produced from chia and flaxseed mucilage: Characterization, stability and antimicrobial activity against Salmonella and Listeria monocytogenes. Food Microbiol. 2022 Dec;108:104116. doi: 10.1016/j.fm.2022.104116. Epub 2022 Aug 18. [PubMed:36088121 ]
Liu X, Li Y, Micallef SA: Developmentally related and drought-induced shifts in the kale metabolome limited Salmonella enterica association, providing novel insights to enhance food safety. Food Microbiol. 2022 Dec;108:104113. doi: 10.1016/j.fm.2022.104113. Epub 2022 Aug 18. [PubMed:36088120 ]
Dos Santos AMP, Panzenhagen P, Ferrari RG, Conte-Junior CA: Large-scale genomic analysis reveals the pESI-like megaplasmid presence in Salmonella Agona, Muenchen, Schwarzengrund, and Senftenberg. Food Microbiol. 2022 Dec;108:104112. doi: 10.1016/j.fm.2022.104112. Epub 2022 Aug 12. [PubMed:36088119 ]
LOTUS database [Link]

Showing NP-Card for {5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate (NP0238299)

MOL for NP0238299 ({5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate)

3D MOL for NP0238299 ({5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate)

3D SDF for NP0238299 ({5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate)

3D-SDF for NP0238299 ({5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate)

PDB for NP0238299 ({5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate)

3D PDB for NP0238299 ({5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate)

SMILES for NP0238299 ({5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate)

INCHI for NP0238299 ({5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate)

Structure for NP0238299 ({5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate)

3D Structure for NP0238299 ({5-methyl-4,9-dioxonaphtho[2,3-b]furan-3-yl}methyl formate)