NP-MRD: Showing NP-Card for 4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid (NP0160644)

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Record Information

Version

2.0

Created at

2022-09-02 18:38:35 UTC

Updated at

2022-09-02 18:38:35 UTC

NP-MRD ID

NP0160644

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid

Description

4-[11-(2-Carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]Pentadec-2(10)-en-6-yl]pentanoic acid belongs to the class of organic compounds known as carbocyclic fatty acids. These are fatty acids containing a carbocyclic ring. 4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid is found in Ganoderma fornicatum. 4-[11-(2-Carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]Pentadec-2(10)-en-6-yl]pentanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181500132D          

 34 37  0  0  0  0            999 V2000
    5.1045    2.5113    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


  Mrv1533004181500132D          

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  8 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 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
 24 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 13 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160644

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC(O)=O)C1CCC2(C)C3=C(C(=O)CC12C)C(C)(CCC(O)=O)C1CC3OC1(C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O7/c1-15(6-7-20(30)31)16-8-11-25(3)23-18-12-19(27(5,14-28)34-18)24(2,10-9-21(32)33)22(23)17(29)13-26(16,25)4/h15-16,18-19,28H,6-14H2,1-5H3,(H,30,31)(H,32,33)

> <INCHI_KEY>
IABFUGDOHOVCEJ-UHFFFAOYSA-N

> <FORMULA>
C27H40O7

> <MOLECULAR_WEIGHT>
476.61

> <EXACT_MASS>
476.277403628

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.60158063772411

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
2.958208782999998

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.746806387368907

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.14099212257337

> <JCHEM_PKA_STRONGEST_BASIC>
-3.076988286182285

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
125.6889

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.97e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       9.528   4.688   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.537   3.148   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.875   2.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.205   3.163   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.543   2.401   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.872   3.178   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      13.551   0.861   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.208   2.370   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.056   0.838   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.551   0.509   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.774   1.838   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.875   0.587   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.265   2.150   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.781   3.612   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.805   4.762   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.321   6.224   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.313   4.451   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.798   2.989   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.936   4.026   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.336   4.145   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.177   5.435   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.266   5.252   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.228   4.878   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.299   5.985   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.793   5.612   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.875   7.466   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.019   3.348   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.911   1.803   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.424   0.860   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.891   0.713   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.821   1.820   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.262   0.725   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.702   2.053   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.262   3.487   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   18                                             
CONECT   12   11                                                            
CONECT   13   11   14   29                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    8   11   19                                             
CONECT   19   18                                                            
CONECT   20   14   21   22   27                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   20   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   13   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   27   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
4-[11-(2-Carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0,.0,]pentadec-2(10)-en-6-yl]pentanoate	Generator
4-[11-(2-Carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoate	Generator

Chemical Formula

C₂₇H₄₀O₇

Average Mass

476.6100 Da

Monoisotopic Mass

476.27740 Da

IUPAC Name

4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid

Traditional Name

4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC(O)=O)C1CCC2(C)C3=C(C(=O)CC12C)C(C)(CCC(O)=O)C1CC3OC1(C)CO

InChI Identifier

InChI=1S/C27H40O7/c1-15(6-7-20(30)31)16-8-11-25(3)23-18-12-19(27(5,14-28)34-18)24(2,10-9-21(32)33)22(23)17(29)13-26(16,25)4/h15-16,18-19,28H,6-14H2,1-5H3,(H,30,31)(H,32,33)

InChI Key

IABFUGDOHOVCEJ-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
Ganoderma fornicatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbocyclic fatty acids. These are fatty acids containing a carbocyclic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Carbocyclic fatty acids

Alternative Parents

Substituents

Carbocyclic fatty acid
Branched fatty acid
Cyclohexenone
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Short-chain hydroxy acid
Dicarboxylic acid or derivatives
Tetrahydrofuran
Ketone
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Primary alcohol
Organooxygen compound
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	3.19	ALOGPS
logP	2.96	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	125.69 m³·mol⁻¹	ChemAxon
Polarizability	52.6 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid (NP0160644)

MOL for NP0160644 (4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid)

3D MOL for NP0160644 (4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid)

3D SDF for NP0160644 (4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid)

3D-SDF for NP0160644 (4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid)

PDB for NP0160644 (4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid)

3D PDB for NP0160644 (4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid)

SMILES for NP0160644 (4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid)

INCHI for NP0160644 (4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid)

Structure for NP0160644 (4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid)

3D Structure for NP0160644 (4-[11-(2-carboxyethyl)-13-(hydroxymethyl)-3,7,11,13-tetramethyl-9-oxo-14-oxatetracyclo[10.2.1.0²,¹⁰.0³,⁷]pentadec-2(10)-en-6-yl]pentanoic acid)