NP-MRD: Showing NP-Card for Cytochalasin Qpho (NP0058046)

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Record Information

Version

2.0

Created at

2022-04-28 03:22:52 UTC

Updated at

2022-04-28 03:22:52 UTC

NP-MRD ID

NP0058046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cytochalasin Qpho

Description

SCHEMBL33816 belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K. Cytochalasin Qpho is found in Phomopsis sp. Based on a literature review very few articles have been published on SCHEMBL33816.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205222D          

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M  END

     RDKit          3D

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M  END
> <DATABASE_ID>
NP0058046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)NC(=O)[C@@]22[C@@H](\C=C\C[C@H](C)C[C@@](C)(O)\C=C\[C@H]2O)[C@H](O)[C@@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO5/c1-17-9-8-12-20-24(31)27(4,34)18(2)23-21(15-19-10-6-5-7-11-19)29-25(32)28(20,23)22(30)13-14-26(3,33)16-17/h5-8,10-14,17-18,20-24,30-31,33-34H,9,15-16H2,1-4H3,(H,29,32)/b12-8+,14-13+/t17-,18-,20-,21-,22+,23-,24-,26-,27-,28+/m0/s1

> <INCHI_KEY>
KPQRGEZMOJERCR-KEYAGYRUSA-N

> <FORMULA>
C28H39NO5

> <MOLECULAR_WEIGHT>
469.622

> <EXACT_MASS>
469.28282336

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.03520935934208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,5S,6S,6aR,10S,12R,15R,15aR,15bR)-3-benzyl-5,6,12,15-tetrahydroxy-4,5,10,12-tetramethyl-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-1-one

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.1178696446666674

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.9210269013799

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.300459331577773

> <JCHEM_PKA_STRONGEST_BASIC>
-0.31451069460287295

> <JCHEM_POLAR_SURFACE_AREA>
110.02000000000001

> <JCHEM_REFRACTIVITY>
133.55679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,5S,6S,6aR,10S,12R,15R,15aR,15bR)-3-benzyl-5,6,12,15-tetrahydroxy-4,5,10,12-tetramethyl-2H,3H,4H,6H,6aH,9H,10H,11H,15H,15bH-cycloundeca[e]isoindol-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.277  -7.228   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.083  -6.505   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.389  -7.321   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.335  -8.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.976  -9.583   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.330  -8.767   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.748  -6.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.802  -5.058   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.588  -4.110   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.115  -2.663   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.253  -1.387   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.654  -2.717   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.854  -3.824   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.348  -4.196   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.642  -3.461   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.844  -2.205   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.723  -1.609   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.375  -1.945   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.734  -1.221   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.842  -2.291   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.167  -3.675   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.561  -5.314   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.492  -6.422   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.998  -6.049   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.696  -4.774   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.202  -4.402   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.152  -5.529   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.562  -7.529   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.172  -7.928   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.698  -3.842   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.287  -0.873   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.787  -4.491   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.137  -3.088   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.787  -5.517   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17   26                                             
CONECT   13   12    8   14                                                  
CONECT   14   13   15   34                                                  
CONECT   15   14   16   32   33                                             
CONECT   16   15   17   31                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28   29                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   12   27                                                  
CONECT   27   26                                                            
CONECT   28   23                                                            
CONECT   29   23                                                            
CONECT   30   21                                                            
CONECT   31   16                                                            
CONECT   32   15                                                            
CONECT   33   15                                                            
CONECT   34   14                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₉NO₅

Average Mass

469.6220 Da

Monoisotopic Mass

469.28282 Da

IUPAC Name

(3S,4S,5S,6S,6aR,10S,12R,15R,15aR,15bR)-3-benzyl-5,6,12,15-tetrahydroxy-4,5,10,12-tetramethyl-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-1-one

Traditional Name

(3S,4S,5S,6S,6aR,10S,12R,15R,15aR,15bR)-3-benzyl-5,6,12,15-tetrahydroxy-4,5,10,12-tetramethyl-2H,3H,4H,6H,6aH,9H,10H,11H,15H,15bH-cycloundeca[e]isoindol-1-one

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)NC(=O)[C@@]22[C@@H](\C=C\C[C@H](C)C[C@@](C)(O)\C=C\[C@H]2O)[C@H](O)[C@@]1(C)O

InChI Identifier

InChI=1S/C28H39NO5/c1-17-9-8-12-20-24(31)27(4,34)18(2)23-21(15-19-10-6-5-7-11-19)29-25(32)28(20,23)22(30)13-14-26(3,33)16-17/h5-8,10-14,17-18,20-24,30-31,33-34H,9,15-16H2,1-4H3,(H,29,32)/b12-8+,14-13+/t17-,18-,20-,21-,22+,23-,24-,26-,27-,28+/m0/s1

InChI Key

KPQRGEZMOJERCR-KEYAGYRUSA-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
Phomopsis sp. Phomopsis sp.	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cytochalasans

Sub Class

Not Available

Direct Parent

Cytochalasans

Alternative Parents

Substituents

Carbocyclic cytochalasan skeleton
Cytochalasan
Isoindolone
Isoindoline
Isoindole
Isoindole or derivatives
Monocyclic benzene moiety
Benzenoid
Pyrrolidone
2-pyrrolidone
Cyclic alcohol
Pyrrolidine
Tertiary alcohol
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
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	2.53	ALOGPS
logP	2.12	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.3	ChemAxon
pKa (Strongest Basic)	-0.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.02 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.56 m³·mol⁻¹	ChemAxon
Polarizability	52.04 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	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

10313324

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14286480

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cytochalasin Qpho (NP0058046)

MOL for NP0058046 (Cytochalasin Qpho)

3D MOL for NP0058046 (Cytochalasin Qpho)

3D SDF for NP0058046 (Cytochalasin Qpho)

3D-SDF for NP0058046 (Cytochalasin Qpho)

PDB for NP0058046 (Cytochalasin Qpho)

3D PDB for NP0058046 (Cytochalasin Qpho)

SMILES for NP0058046 (Cytochalasin Qpho)

INCHI for NP0058046 (Cytochalasin Qpho)

Structure for NP0058046 (Cytochalasin Qpho)

3D Structure for NP0058046 (Cytochalasin Qpho)