NP-MRD: Showing NP-Card for (+)-Boletocrocin A (NP0077539)

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Record Information

Version

2.0

Created at

2022-04-28 22:40:28 UTC

Updated at

2022-04-28 22:40:28 UTC

NP-MRD ID

NP0077539

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Boletocrocin A

Description

Boletocrocin A belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (+)-Boletocrocin A is found in Boletus laetissimus Hongo and Crocinoboletus laetissimus. Based on a literature review very few articles have been published on Boletocrocin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200402D          

 36 35  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292200402D          

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M  END
> <DATABASE_ID>
NP0077539

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@H](NC(=O)\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C(=O)N[C@@H](CC(O)=O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32N2O8/c1-3-19(2)24(26(35)36)28-22(30)17-15-13-11-9-7-5-4-6-8-10-12-14-16-21(29)27-20(25(33)34)18-23(31)32/h4-17,19-20,24H,3,18H2,1-2H3,(H,27,29)(H,28,30)(H,31,32)(H,33,34)(H,35,36)/b5-4+,8-6+,9-7+,12-10+,13-11+,16-14+,17-15+/t19-,20-,24-/m0/s1

> <INCHI_KEY>
OTBWMESMPGYGIA-GHHGTSARSA-N

> <FORMULA>
C26H32N2O8

> <MOLECULAR_WEIGHT>
500.548

> <EXACT_MASS>
500.215865998

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.216412543129266

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2E,4E,6E,8E,10E,12E,14E)-15-{[(1S,2S)-1-carboxy-2-methylbutyl]carbamoyl}pentadeca-2,4,6,8,10,12,14-heptaenamido]butanedioic acid

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
2.739593690333332

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.27239621754976

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5225199344303824

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3437485848980367

> <JCHEM_POLAR_SURFACE_AREA>
170.1

> <JCHEM_REFRACTIVITY>
140.74540000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.87e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2E,4E,6E,8E,10E,12E,14E)-15-{[(1S,2S)-1-carboxy-2-methylbutyl]carbamoyl}pentadeca-2,4,6,8,10,12,14-heptaenamido]butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -8.717  24.227   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -8.717  25.767   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -7.383  23.457   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.383  21.917   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -6.049  21.147   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -6.049  19.607   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.383  18.837   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.716  18.837   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.716  17.297   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.382  16.527   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.382  14.987   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.048  14.217   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.048  12.677   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.715  11.907   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.715  10.367   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.619   9.597   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.619   8.057   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.953   7.287   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.953   5.747   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.286   4.977   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       5.954   3.437   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.288   3.437   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.621   4.977   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.287   1.127   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.621   0.357   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.954   0.357   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -8.717  21.147   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -8.717  19.607   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0     -10.050  21.917   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -10.050  23.457   0.000  0.00  0.00           O+0
CONECT    1    2    3   36                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26                                                            
CONECT   30   25   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    4   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36    1                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂N₂O₈

Average Mass

500.5480 Da

Monoisotopic Mass

500.21587 Da

IUPAC Name

(2S)-2-[(2E,4E,6E,8E,10E,12E,14E)-15-{[(1S,2S)-1-carboxy-2-methylbutyl]carbamoyl}pentadeca-2,4,6,8,10,12,14-heptaenamido]butanedioic acid

Traditional Name

(2S)-2-[(2E,4E,6E,8E,10E,12E,14E)-15-{[(1S,2S)-1-carboxy-2-methylbutyl]carbamoyl}pentadeca-2,4,6,8,10,12,14-heptaenamido]butanedioic acid

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@H](NC(=O)\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C(=O)N[C@@H](CC(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C26H32N2O8/c1-3-19(2)24(26(35)36)28-22(30)17-15-13-11-9-7-5-4-6-8-10-12-14-16-21(29)27-20(25(33)34)18-23(31)32/h4-17,19-20,24H,3,18H2,1-2H3,(H,27,29)(H,28,30)(H,31,32)(H,33,34)(H,35,36)/b5-4+,8-6+,9-7+,12-10+,13-11+,16-14+,17-15+/t19-,20-,24-/m0/s1

InChI Key

OTBWMESMPGYGIA-GHHGTSARSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Boletus laetissimus Hongo	Fungi	KNApSAcK
Crocinoboletus laetissimus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine 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

Isoleucine and derivatives

Alternative Parents

Substituents

Isoleucine or derivatives
Aspartic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Tricarboxylic acid or derivatives
N-acyl-amine
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	3.11	ALOGPS
logP	2.74	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	3.52	ChemAxon
pKa (Strongest Basic)	-0.34	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.1 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	140.75 m³·mol⁻¹	ChemAxon
Polarizability	55.22 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	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

C00040899

Chemspider ID

78437381

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100927521

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Boletocrocin A (NP0077539)

MOL for NP0077539 ((+)-Boletocrocin A)

3D MOL for NP0077539 ((+)-Boletocrocin A)

3D SDF for NP0077539 ((+)-Boletocrocin A)

3D-SDF for NP0077539 ((+)-Boletocrocin A)

PDB for NP0077539 ((+)-Boletocrocin A)

3D PDB for NP0077539 ((+)-Boletocrocin A)

SMILES for NP0077539 ((+)-Boletocrocin A)

INCHI for NP0077539 ((+)-Boletocrocin A)

Structure for NP0077539 ((+)-Boletocrocin A)

3D Structure for NP0077539 ((+)-Boletocrocin A)