NP-MRD: Showing NP-Card for (3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid (NP0252841)

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Record Information

Version

2.0

Created at

2022-09-07 16:29:53 UTC

Updated at

2022-09-07 16:29:53 UTC

NP-MRD ID

NP0252841

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid

Description

CHEBI:144193 Belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof. (3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid is found in Lepra amara. Based on a literature review very few articles have been published on CHEBI:144193.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072218292D          

 32 34  0  0  1  0            999 V2000
    2.4688    5.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6914    4.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0878    3.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2262    2.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0240    1.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2020    0.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0243    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3779   -0.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1047   -0.6995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9091   -0.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0868   -0.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940   -1.4276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8810   -2.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7333   -0.0902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1961   -0.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8963   -1.6603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346   -0.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5011    0.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1705    1.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5292    2.3078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9732    2.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7523    2.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603    3.1522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2838    3.6600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5398    1.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5805    1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4682    0.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3037    0.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072218292D          

 32 34  0  0  1  0            999 V2000
    2.4688    5.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6914    4.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0878    3.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2262    2.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0240    1.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2020    0.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0243    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3779   -0.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4682    0.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0252841

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1=CC(=O)C=C(OC)[C@@]11C(=O)OC2=CC(O)=C(C(O)=O)C(CCCCC)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O7/c1-4-6-8-10-15-12-16(26)13-20(31-3)25(15)22-17(11-9-7-5-2)21(23(28)29)18(27)14-19(22)32-24(25)30/h12-14,27H,4-11H2,1-3H3,(H,28,29)/t25-/m0/s1

> <INCHI_KEY>
LOGCRVAWKCZXQM-VWLOTQADSA-N

> <FORMULA>
C25H30O7

> <MOLECULAR_WEIGHT>
442.508

> <EXACT_MASS>
442.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.13596661573357

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentyl-2H-spiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid

> <JCHEM_LOGP>
5.986340778333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.158193620363202

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7505321140993795

> <JCHEM_PKA_STRONGEST_BASIC>
-4.817704894822848

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
121.77039999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.609   9.418   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.024   7.935   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.897   6.783   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.156   4.891   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.778   3.049   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.110   1.099   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.645   0.975   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.305  -0.417   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.662  -1.306   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.430  -1.684   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.895  -1.560   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.789  -2.665   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.511  -4.130   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.235  -0.168   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.233  -1.337   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.673  -3.099   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.811  -0.745   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.935   0.790   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.122   1.910   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.318   3.385   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.988   4.308   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.817   3.741   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.404   5.406   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.913   5.884   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.530   6.832   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.874   2.622   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.817   2.255   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.474   1.373   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.113   1.665   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.654   1.373   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.659   2.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.434   1.146   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11    6   15   32                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   32                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   22   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   26   18   14                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀O₇

Average Mass

442.5080 Da

Monoisotopic Mass

442.19915 Da

IUPAC Name

(3R)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentyl-2H-spiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid

Traditional Name

(3R)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCCC1=CC(=O)C=C(OC)[C@@]11C(=O)OC2=CC(O)=C(C(O)=O)C(CCCCC)=C12

InChI Identifier

InChI=1S/C25H30O7/c1-4-6-8-10-15-12-16(26)13-20(31-3)25(15)22-17(11-9-7-5-2)21(23(28)29)18(27)14-19(22)32-24(25)30/h12-14,27H,4-11H2,1-3H3,(H,28,29)/t25-/m0/s1

InChI Key

LOGCRVAWKCZXQM-VWLOTQADSA-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
Lepra amara	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acid and derivatives

Alternative Parents

Substituents

Salicylic acid or derivatives
Benzofuran
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous ester
Vinylogous acid
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxide
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	5.99	ChemAxon
pKa (Strongest Acidic)	2.75	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	121.77 m³·mol⁻¹	ChemAxon
Polarizability	47.14 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

34993230

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90478746

PDB ID

Not Available

ChEBI ID

144193

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid (NP0252841)

MOL for NP0252841 ((3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid)

3D MOL for NP0252841 ((3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid)

3D SDF for NP0252841 ((3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid)

3D-SDF for NP0252841 ((3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid)

PDB for NP0252841 ((3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid)

3D PDB for NP0252841 ((3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid)

SMILES for NP0252841 ((3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid)

INCHI for NP0252841 ((3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid)

Structure for NP0252841 ((3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid)

3D Structure for NP0252841 ((3r)-6-hydroxy-2'-methoxy-2,4'-dioxo-4,6'-dipentylspiro[1-benzofuran-3,1'-cyclohexane]-2',5'-diene-5-carboxylic acid)