NP-MRD: Showing NP-Card for 4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid (NP0313270)

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Record Information

Version

2.0

Created at

2022-09-11 10:42:04 UTC

Updated at

2022-09-11 10:42:04 UTC

NP-MRD ID

NP0313270

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid

Description

4-Hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-1H,3H,4H,5H,8H,9H,10H-cyclonona[c]furan-6,7-dicarboxylic acid belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. 4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid is found in Talaromyces purpureogenus. Based on a literature review very few articles have been published on 4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-1H,3H,4H,5H,8H,9H,10H-cyclonona[c]furan-6,7-dicarboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112212422D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309112212422D          

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    5.3560   -7.7584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5469   -5.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344   -5.5726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 22 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 37  1  0  0  0  0
  9 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0313270

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC(O)C1C(O)C2=C(CC(CC(C(O)=O)=C1C(O)=O)C(O)C1CC=CC(=O)C1)C(=O)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O11/c1-2-3-4-5-9-18(29)21-19(25(34)35)16(24(32)33)11-14(22(30)13-7-6-8-15(28)10-13)12-17-20(23(21)31)27(37)38-26(17)36/h6,8,13-14,18,21-23,29-31H,2-5,7,9-12H2,1H3,(H,32,33)(H,34,35)

> <INCHI_KEY>
LZANHLRQWLRERF-UHFFFAOYSA-N

> <FORMULA>
C27H34O11

> <MOLECULAR_WEIGHT>
534.558

> <EXACT_MASS>
534.210111915

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.18769415239723

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-1H,3H,4H,5H,8H,9H,10H-cyclonona[c]furan-6,7-dicarboxylic acid

> <JCHEM_LOGP>
1.995691093

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.435703109244815

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.744273938612843

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8991440212442043

> <JCHEM_POLAR_SURFACE_AREA>
195.72999999999996

> <JCHEM_REFRACTIVITY>
133.14759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4H,5H,8H,9H,10H-cyclonona[c]furan-6,7-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.447  -7.848   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.114  -8.618   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.220  -7.848   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.554  -8.618   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.887  -7.848   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.221  -8.618   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.555  -7.848   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.555  -6.308   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.888  -8.618   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.068  -7.628   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.541  -6.181   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.531  -5.001   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.025  -5.914   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.608  -7.628   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.135  -6.181   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.651  -5.914   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.145  -5.001   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.788  -8.618   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.055 -10.135   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.572 -10.402   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.562  -9.222   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.098 -11.849   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.615 -12.117   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.142 -13.564   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.152 -14.744   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.635 -14.476   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.645 -15.656   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.109 -13.029   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.285 -11.468   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.838 -11.995   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.391 -11.468   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.443 -12.682   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.904 -12.628   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       7.304 -13.959   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.784 -13.534   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.998 -14.482   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.621 -10.135   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.104 -10.402   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   37                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19                                                       
CONECT   19   18   20   29                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   22                                                       
CONECT   29   19   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   37                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   30   36                                                  
CONECT   36   35                                                            
CONECT   37   31    9   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-1H,3H,4H,5H,8H,9H,10H-cyclonona[c]furan-6,7-dicarboxylate	Generator

Chemical Formula

C₂₇H₃₄O₁₁

Average Mass

534.5580 Da

Monoisotopic Mass

534.21011 Da

IUPAC Name

4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-1H,3H,4H,5H,8H,9H,10H-cyclonona[c]furan-6,7-dicarboxylic acid

Traditional Name

4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4H,5H,8H,9H,10H-cyclonona[c]furan-6,7-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCCCC(O)C1C(O)C2=C(CC(CC(C(O)=O)=C1C(O)=O)C(O)C1CC=CC(=O)C1)C(=O)OC2=O

InChI Identifier

InChI=1S/C27H34O11/c1-2-3-4-5-9-18(29)21-19(25(34)35)16(24(32)33)11-14(22(30)13-7-6-8-15(28)10-13)12-17-20(23(21)31)27(37)38-26(17)36/h6,8,13-14,18,21-23,29-31H,2-5,7,9-12H2,1H3,(H,32,33)(H,34,35)

InChI Key

LZANHLRQWLRERF-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

Species Name	Source	Reference
Penicillium purpurogenum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Fatty alcohol
Cyclohexenone
Fatty acyl
2-furanone
Dihydrofuran
Carboxylic acid anhydride
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	ChemAxon
pKa (Strongest Acidic)	3.74	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	195.73 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	133.15 m³·mol⁻¹	ChemAxon
Polarizability	54.19 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

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

162814061

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid (NP0313270)

MOL for NP0313270 (4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid)

3D MOL for NP0313270 (4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid)

3D SDF for NP0313270 (4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid)

3D-SDF for NP0313270 (4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid)

PDB for NP0313270 (4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid)

3D PDB for NP0313270 (4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid)

SMILES for NP0313270 (4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid)

INCHI for NP0313270 (4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid)

Structure for NP0313270 (4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid)

3D Structure for NP0313270 (4-hydroxy-9-[hydroxy(5-oxocyclohex-3-en-1-yl)methyl]-5-(1-hydroxyheptyl)-1,3-dioxo-4h,5h,8h,9h,10h-cyclonona[c]furan-6,7-dicarboxylic acid)