NP-MRD: Showing NP-Card for (2s)-2-[(2r,2'r,4'as,6's,7'r,8'as)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl]-3-methylbutanoic acid (NP0204740)

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Record Information

Version

2.0

Created at

2022-09-05 00:28:35 UTC

Updated at

2022-09-05 00:28:35 UTC

NP-MRD ID

NP0204740

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-[(2r,2'r,4'as,6's,7'r,8'as)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl]-3-methylbutanoic acid

Description

ZINC31164521 belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on ZINC31164521.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052202282D          

 36 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309052202282D          

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  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 24 33  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  1  0  0  0
 11 35  1  0  0  0  0
  8 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0204740

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H](N1CC2=C(C=C(O)C3=C2O[C@]2(C3)[C@H](C)CC[C@H]3C(C)(C)[C@H](O)[C@H](O)C[C@]23C)C1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO7/c1-13(2)21(25(34)35)29-12-17-15(24(29)33)9-18(30)16-10-28(36-22(16)17)14(3)7-8-20-26(4,5)23(32)19(31)11-27(20,28)6/h9,13-14,19-21,23,30-32H,7-8,10-12H2,1-6H3,(H,34,35)/t14-,19-,20+,21+,23-,27+,28-/m1/s1

> <INCHI_KEY>
JJWKFIISZGZPHY-VJKHVDRLSA-N

> <FORMULA>
C28H39NO7

> <MOLECULAR_WEIGHT>
501.62

> <EXACT_MASS>
501.2726526

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.50681758242668

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2R,2'R,4'aS,6'S,7'R,8'aS)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,5',6,6',7,7',8,8',8'a-dodecahydro-2'H-spiro[furo[2,3-e]isoindole-2,1'-naphthalene]-7-yl]-3-methylbutanoic acid

> <JCHEM_LOGP>
3.3601280480000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.944927966113484

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1241038776375825

> <JCHEM_PKA_STRONGEST_BASIC>
-1.682794246056107

> <JCHEM_POLAR_SURFACE_AREA>
127.53

> <JCHEM_REFRACTIVITY>
132.9064

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2R,2'R,4'aS,6'S,7'R,8'aS)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'H-spiro[furo[2,3-e]isoindole-2,1'-naphthalene]-7-yl]-3-methylbutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      14.592  -0.078   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.181   0.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.011   2.070   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.941  -0.373   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.111  -1.904   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.871  -2.817   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      13.522  -2.521   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      10.530   0.245   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.201  -0.534   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.051   0.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.668   1.900   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.755   3.141   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.225   2.970   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.312   4.211   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.607   1.560   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.520   0.319   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.623  -0.932   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.155  -0.465   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.146   1.075   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.326  -1.996   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.736  -2.614   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.085  -2.909   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.675  -2.291   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.504  -0.761   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.093  -0.143   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.270  -1.639   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.443  -0.045   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.077   1.388   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.488   2.005   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.163   2.301   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.993   3.831   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.574   1.683   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.744   0.152   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.642   1.404   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.201   1.749   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.224   2.900   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9   35                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   19                                                  
CONECT   16   15   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   33                                             
CONECT   19   18   15                                                       
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   24   18   34                                             
CONECT   34   33                                                            
CONECT   35   11    8   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₉NO₇

Average Mass

501.6200 Da

Monoisotopic Mass

501.27265 Da

IUPAC Name

(2S)-2-[(2R,2'R,4'aS,6'S,7'R,8'aS)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,5',6,6',7,7',8,8',8'a-dodecahydro-2'H-spiro[furo[2,3-e]isoindole-2,1'-naphthalene]-7-yl]-3-methylbutanoic acid

Traditional Name

(2S)-2-[(2R,2'R,4'aS,6'S,7'R,8'aS)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'H-spiro[furo[2,3-e]isoindole-2,1'-naphthalene]-7-yl]-3-methylbutanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](N1CC2=C(C=C(O)C3=C2O[C@]2(C3)[C@H](C)CC[C@H]3C(C)(C)[C@H](O)[C@H](O)C[C@]23C)C1=O)C(O)=O

InChI Identifier

InChI=1S/C28H39NO7/c1-13(2)21(25(34)35)29-12-17-15(24(29)33)9-18(30)16-10-28(36-22(16)17)14(3)7-8-20-26(4,5)23(32)19(31)11-27(20,28)6/h9,13-14,19-21,23,30-32H,7-8,10-12H2,1-6H3,(H,34,35)/t14-,19-,20+,21+,23-,27+,28-/m1/s1

InChI Key

JJWKFIISZGZPHY-VJKHVDRLSA-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 valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Valine and derivatives

Alternative Parents

Substituents

Valine or derivatives
Isoindolone
Isoindole
Isoindole or derivatives
Isoindoline
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Cyclic alcohol
Tertiary carboxylic acid amide
Lactam
Secondary alcohol
1,2-diol
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Ether
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Alcohol
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	3.36	ChemAxon
pKa (Strongest Acidic)	3.12	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	127.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	132.91 m³·mol⁻¹	ChemAxon
Polarizability	54.51 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

78442695

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

38357959

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-[(2r,2'r,4'as,6's,7'r,8'as)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl]-3-methylbutanoic acid (NP0204740)

MOL for NP0204740 ((2s)-2-[(2r,2'r,4'as,6's,7'r,8'as)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl]-3-methylbutanoic acid)

3D MOL for NP0204740 ((2s)-2-[(2r,2'r,4'as,6's,7'r,8'as)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl]-3-methylbutanoic acid)

3D SDF for NP0204740 ((2s)-2-[(2r,2'r,4'as,6's,7'r,8'as)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl]-3-methylbutanoic acid)

3D-SDF for NP0204740 ((2s)-2-[(2r,2'r,4'as,6's,7'r,8'as)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl]-3-methylbutanoic acid)

PDB for NP0204740 ((2s)-2-[(2r,2'r,4'as,6's,7'r,8'as)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl]-3-methylbutanoic acid)

3D PDB for NP0204740 ((2s)-2-[(2r,2'r,4'as,6's,7'r,8'as)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl]-3-methylbutanoic acid)

SMILES for NP0204740 ((2s)-2-[(2r,2'r,4'as,6's,7'r,8'as)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl]-3-methylbutanoic acid)

INCHI for NP0204740 ((2s)-2-[(2r,2'r,4'as,6's,7'r,8'as)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl]-3-methylbutanoic acid)

Structure for NP0204740 ((2s)-2-[(2r,2'r,4'as,6's,7'r,8'as)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl]-3-methylbutanoic acid)

3D Structure for NP0204740 ((2s)-2-[(2r,2'r,4'as,6's,7'r,8'as)-4,6',7'-trihydroxy-2',5',5',8'a-tetramethyl-6-oxo-3,3',4',4'a,6',7',8,8'-octahydro-2'h-spiro[furo[2,3-e]isoindole-2,1'-naphthalen]-7-yl]-3-methylbutanoic acid)