NP-MRD: Showing NP-Card for callystatin a (NP0302731)

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Record Information

Version

2.0

Created at

2022-09-10 16:30:10 UTC

Updated at

2022-09-10 16:30:11 UTC

NP-MRD ID

NP0302731

Secondary Accession Numbers

None

Natural Product Identification

Common Name

callystatin a

Description

Callystatin A belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. callystatin a was first documented in 2006 (PMID: 16506734). Based on a literature review a small amount of articles have been published on Callystatin A (PMID: 25827465) (PMID: 23019072) (PMID: 22286400) (PMID: 18767199).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102218302D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102218302D          

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M  END
> <DATABASE_ID>
NP0302731

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)\C=C(/C)\C=C\C[C@@H](C)\C=C(\CC)/C=C/[C@H]1CC=CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O4/c1-8-22(5)28(31)24(7)29(32)23(6)18-20(3)12-10-13-21(4)19-25(9-2)16-17-26-14-11-15-27(30)33-26/h10-12,15-19,21-24,26,28,31H,8-9,13-14H2,1-7H3/b12-10+,17-16+,20-18+,25-19-/t21-,22+,23-,24+,26-,28-/m1/s1

> <INCHI_KEY>
QPJTWGLLJWBDQW-KMMMXHTBSA-N

> <FORMULA>
C29H44O4

> <MOLECULAR_WEIGHT>
456.667

> <EXACT_MASS>
456.323959897

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.85610790326059

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-6-[(1E,3Z,5R,7E,9E,11R,13S,14R,15S)-3-ethyl-14-hydroxy-5,9,11,13,15-pentamethyl-12-oxoheptadeca-1,3,7,9-tetraen-1-yl]-5,6-dihydro-2H-pyran-2-one

> <JCHEM_LOGP>
7.400351917

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.716319726540945

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.466652066178856

> <JCHEM_PKA_STRONGEST_BASIC>
-3.001446426903515

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
141.76370000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
callystatin A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      17.338  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.672  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.339  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25    3   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   27                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

View in JSmol

Synonyms

Value	Source
20-Epi-callystatin a	MeSH

Chemical Formula

C₂₉H₄₄O₄

Average Mass

456.6670 Da

Monoisotopic Mass

456.32396 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)\C=C(/C)\C=C\C[C@@H](C)\C=C(\CC)/C=C/[C@H]1CC=CC(=O)O1

InChI Identifier

InChI=1S/C29H44O4/c1-8-22(5)28(31)24(7)29(32)23(6)18-20(3)12-10-13-21(4)19-25(9-2)16-17-26-14-11-15-27(30)33-26/h10-12,15-19,21-24,26,28,31H,8-9,13-14H2,1-7H3/b12-10+,17-16+,20-18+,25-19-/t21-,22+,23-,24+,26-,28-/m1/s1

InChI Key

QPJTWGLLJWBDQW-KMMMXHTBSA-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 diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Long chain fatty alcohol
Fatty alcohol
Dihydropyranone
Fatty acyl
Beta-hydroxy ketone
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

diterpenoid (CHEBI:80782 )

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

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

4581330

KEGG Compound ID

C16891

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Callystatin A

METLIN ID

Not Available

PubChem Compound

5471086

PDB ID

Not Available

ChEBI ID

80782

Good Scents ID

Not Available

References

General References

Raghavan S, Rajendar S: Stereoselective synthesis of the C13-C22 fragment of callystatin A by a non-aldol approach. Org Biomol Chem. 2015 May 7;13(17):5044-53. doi: 10.1039/c5ob00413f. [PubMed:25827465 ]
Candy M, Tomas L, Parat S, Heran V, Bienayme H, Pons JM, Bressy C: A convergent approach to (-)-callystatin A based on local symmetry. Chemistry. 2012 Nov 5;18(45):14267-71. doi: 10.1002/chem.201202701. Epub 2012 Sep 27. [PubMed:23019072 ]
Pujari SA, Kaliappan KP: An iterative Shimizu non-aldol approach for the stereoselective synthesis of C13-C22 fragment of callystatin A. Org Biomol Chem. 2012 Mar 7;10(9):1750-3. doi: 10.1039/c2ob06838a. Epub 2012 Jan 27. [PubMed:22286400 ]
Reichard HA, Rieger JC, Micalizio GC: Total synthesis of callystatin a by titanium-mediated reductive alkyne-alkyne cross-coupling. Angew Chem Int Ed Engl. 2008;47(41):7837-40. doi: 10.1002/anie.200803031. [PubMed:18767199 ]
Liang B, Novak T, Tan Z, Negishi E: Catalytic, efficient, and syn-selective construction of deoxypolypropionates and other chiral compounds via Zr-catalyzed asymmetric carboalumination of allyl alcohol. J Am Chem Soc. 2006 Mar 8;128(9):2770-1. doi: 10.1021/ja0530974. [PubMed:16506734 ]
LOTUS database [Link]

Showing NP-Card for callystatin a (NP0302731)

MOL for NP0302731 (callystatin a)

3D MOL for NP0302731 (callystatin a)

3D SDF for NP0302731 (callystatin a)

3D-SDF for NP0302731 (callystatin a)

PDB for NP0302731 (callystatin a)

3D PDB for NP0302731 (callystatin a)

SMILES for NP0302731 (callystatin a)

INCHI for NP0302731 (callystatin a)

Structure for NP0302731 (callystatin a)

3D Structure for NP0302731 (callystatin a)