NP-MRD: Showing NP-Card for 10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid (NP0149981)

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Record Information

Version

2.0

Created at

2022-09-02 05:57:44 UTC

Updated at

2022-09-02 05:57:44 UTC

NP-MRD ID

NP0149981

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid

Description

10-{[7A-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-octahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety. 10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid is found in Aspergillus fumigatus. 10-{[7A-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-octahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161506562D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161506562D          

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M  END
> <DATABASE_ID>
NP0149981

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C2C(O)(COC2(C)C(O)CC=C(C)C)CCC1OC(=O)C=CC=CC=CC=CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O8/c1-18(2)13-14-20(27)25(3)24-23(32-4)19(15-16-26(24,31)17-33-25)34-22(30)12-10-8-6-5-7-9-11-21(28)29/h5-13,19-20,23-24,27,31H,14-17H2,1-4H3,(H,28,29)

> <INCHI_KEY>
CTJMHUNIVHCSLW-UHFFFAOYSA-N

> <FORMULA>
C26H36O8

> <MOLECULAR_WEIGHT>
476.566

> <EXACT_MASS>
476.241018119

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.67550646173104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-octahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.886951432

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.43631074411504

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.884221256197829

> <JCHEM_PKA_STRONGEST_BASIC>
-3.270372627161086

> <JCHEM_POLAR_SURFACE_AREA>
122.52

> <JCHEM_REFRACTIVITY>
131.88490000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       4.787   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.626  -1.532   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.417   0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.949   3.423   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.989   2.786   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.655   2.016   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.989   4.326   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.322   5.096   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.322   6.636   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.989   7.406   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.656   7.406   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.788   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.122  -0.000   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.789   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.123   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.456   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.790   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.124   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.457   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.791   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.125   2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      23.458   1.540   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      22.125   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   20                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   20                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   11    3    7                                                  
CONECT   21    4   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Value	Source
10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-octahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoate	Generator

Chemical Formula

C₂₆H₃₆O₈

Average Mass

476.5660 Da

Monoisotopic Mass

476.24102 Da

IUPAC Name

10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-octahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid

Traditional Name

10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid

CAS Registry Number

Not Available

SMILES

COC1C2C(O)(COC2(C)C(O)CC=C(C)C)CCC1OC(=O)C=CC=CC=CC=CC(O)=O

InChI Identifier

InChI=1S/C26H36O8/c1-18(2)13-14-20(27)25(3)24-23(32-4)19(15-16-26(24,31)17-33-25)34-22(30)12-10-8-6-5-7-9-11-21(28)29/h5-13,19-20,23-24,27,31H,14-17H2,1-4H3,(H,28,29)

InChI Key

CTJMHUNIVHCSLW-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
Aspergillus fumigatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isobenzofurans

Sub Class

Not Available

Direct Parent

Isobenzofurans

Alternative Parents

Substituents

Isobenzofuran
Medium-chain fatty acid
Branched fatty acid
Fatty acid ester
Heterocyclic fatty acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Unsaturated fatty acid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Carboxylic acid ester
Secondary alcohol
Oxacycle
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	3.05	ALOGPS
logP	2.89	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.88	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	131.88 m³·mol⁻¹	ChemAxon
Polarizability	52.68 Å³	ChemAxon
Number of Rings	2	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

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

72980950

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid (NP0149981)

MOL for NP0149981 (10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid)

3D MOL for NP0149981 (10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid)

3D SDF for NP0149981 (10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid)

3D-SDF for NP0149981 (10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid)

PDB for NP0149981 (10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid)

3D PDB for NP0149981 (10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid)

SMILES for NP0149981 (10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid)

INCHI for NP0149981 (10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid)

Structure for NP0149981 (10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid)

3D Structure for NP0149981 (10-{[7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid)