NP-MRD: Showing NP-Card for (2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid (NP0154832)

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Record Information

Version

2.0

Created at

2022-09-02 11:48:14 UTC

Updated at

2022-09-02 11:48:15 UTC

NP-MRD ID

NP0154832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid

Description

(2R)-2-[(9aR)-9a-methyl-3-octanoyl-2,9-dioxo-6-(prop-1-en-1-yl)-2H,7H,9H,9aH-furo[3,2-g]isoquinolin-7-yl]butanedioic acid belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Based on a literature review very few articles have been published on (2R)-2-[(9aR)-9a-methyl-3-octanoyl-2,9-dioxo-6-(prop-1-en-1-yl)-2H,7H,9H,9aH-furo[3,2-g]isoquinolin-7-yl]butanedioic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022213482D          

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M  END

     RDKit          3D

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  Mrv1652309022213482D          

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 27 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154832

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)C1=C2C=C3C=C(\C=C\C)N(C=C3C(=O)[C@]2(C)OC1=O)[C@H](CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H31NO8/c1-4-6-7-8-9-11-21(29)23-19-13-16-12-17(10-5-2)28(20(25(33)34)14-22(30)31)15-18(16)24(32)27(19,3)36-26(23)35/h5,10,12-13,15,20H,4,6-9,11,14H2,1-3H3,(H,30,31)(H,33,34)/b10-5+/t20-,27-/m1/s1

> <INCHI_KEY>
HUIJYERZPWDBIF-IIDJQOACSA-N

> <FORMULA>
C27H31NO8

> <MOLECULAR_WEIGHT>
497.544

> <EXACT_MASS>
497.204966962

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.33289948655014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(9aR)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1E)-prop-1-en-1-yl]-2H,7H,9H,9aH-furo[3,2-g]isoquinolin-7-yl]butanedioic acid

> <ALOGPS_LOGP>
3.62

> <JCHEM_LOGP>
4.0069458483333324

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.507275795166059

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7549009703285714

> <JCHEM_PKA_STRONGEST_BASIC>
-4.859070782083192

> <JCHEM_POLAR_SURFACE_AREA>
138.28

> <JCHEM_REFRACTIVITY>
134.06879999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(9aR)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1E)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.277   9.750   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.801   8.285   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.832   7.141   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.356   5.676   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.849   5.356   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.374   3.891   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.867   3.571   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.391   2.107   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.984   1.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.651   2.250   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.651   3.790   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.317   1.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.017   2.250   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.350   1.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.684   2.250   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.018   1.480   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.351   2.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.685   1.480   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.145  -0.051   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.001  -1.082   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.652  -0.371   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -6.422   0.962   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.327  -0.284   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.928   1.282   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -8.959   0.138   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -8.404   2.747   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.910   3.067   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0     -10.386   4.532   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0     -11.893   4.852   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -12.923   3.708   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -14.429   4.028   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -15.460   2.883   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -14.905   5.492   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -12.368   6.317   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -11.338   7.461   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -13.875   6.637   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   28                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19    9   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21    8   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    6   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27    4   29                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
(2R)-2-[(9AR)-9a-methyl-3-octanoyl-2,9-dioxo-6-(prop-1-en-1-yl)-2H,7H,9H,9ah-furo[3,2-g]isoquinolin-7-yl]butanedioate	Generator

Chemical Formula

C₂₇H₃₁NO₈

Average Mass

497.5440 Da

Monoisotopic Mass

497.20497 Da

IUPAC Name

(2R)-2-[(9aR)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1E)-prop-1-en-1-yl]-2H,7H,9H,9aH-furo[3,2-g]isoquinolin-7-yl]butanedioic acid

Traditional Name

(2R)-2-[(9aR)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1E)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)C1=C2C=C3C=C(\C=C\C)N(C=C3C(=O)[C@]2(C)OC1=O)[C@H](CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C27H31NO8/c1-4-6-7-8-9-11-21(29)23-19-13-16-12-17(10-5-2)28(20(25(33)34)14-22(30)31)15-18(16)24(32)27(19,3)36-26(23)35/h5,10,12-13,15,20H,4,6-9,11,14H2,1-3H3,(H,30,31)(H,33,34)/b10-5+/t20-,27-/m1/s1

InChI Key

HUIJYERZPWDBIF-IIDJQOACSA-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 annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Aspartic acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
D-alpha-amino acid
Tetrahydroisoquinoline
Tricarboxylic acid or derivatives
Cyclohexenone
Dihydropyridine
Alpha-acyloxy ketone
2-furanone
Dihydrofuran
Enoate ester
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Amino acid
Ketone
Lactone
Tertiary amine
Tertiary aliphatic amine
Enamine
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Allylamine
Azacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxide
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	3.62	ALOGPS
logP	4.01	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	138.28 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	134.07 m³·mol⁻¹	ChemAxon
Polarizability	53.33 Å³	ChemAxon
Number of Rings	3	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

8990451

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10815146

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid (NP0154832)

MOL for NP0154832 ((2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid)

3D MOL for NP0154832 ((2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid)

3D SDF for NP0154832 ((2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid)

3D-SDF for NP0154832 ((2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid)

PDB for NP0154832 ((2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid)

3D PDB for NP0154832 ((2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid)

SMILES for NP0154832 ((2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid)

INCHI for NP0154832 ((2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid)

Structure for NP0154832 ((2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid)

3D Structure for NP0154832 ((2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid)