NP-MRD: Showing NP-Card for (±)-Penindolene B (NP0332838)

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Record Information

Version

2.0

Created at

2024-04-23 05:54:20 UTC

Updated at

2024-09-03 04:20:26 UTC

NP-MRD ID

NP0332838

Natural Product DOI

https://doi.org/10.57994/2113

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(±)-Penindolene B

Description

(±)-Penindolene B belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. (±)-Penindolene B was first documented in 2024 (PMID: 38635317). Based on a literature review very few articles have been published on (±)-Penindolene B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01052308312D          

 26 27  0  0  1  0            999 V2000
    6.3235    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821    5.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3071    6.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    6.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    4.7652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0380    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7525    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7525    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0380    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.0527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5620    0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3071   -0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2272    0.5678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4425    0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8294    0.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3467    0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    3.5277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22 18  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 19 25  2  0  0  0  0
 15 26  2  0  0  0  0
M  END


  Mrv2104 01052308312D          

 26 27  0  0  1  0            999 V2000
    6.3235    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821    5.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3071    6.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    6.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    4.7652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0380    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7525    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7525    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0380    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.0527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5620    0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3071   -0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2272    0.5678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4425    0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8294    0.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3467    0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    3.5277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  0  0  0  0
 22 18  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 19 25  2  0  0  0  0
 15 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332838

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1CCC(=O)N1CCC(=O)C1=CC=CC=C1NC(=O)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H26N2O4/c1-5-20(2,3)19(25)21-15-9-7-6-8-14(15)16(23)12-13-22-17(24)10-11-18(22)26-4/h5-9,18H,1,10-13H2,2-4H3,(H,21,25)/t18-/m0/s1

> <INCHI_KEY>
HOXLTIXGFZABJS-SFHVURJKSA-N

> <FORMULA>
C20H26N2O4

> <MOLECULAR_WEIGHT>
358.438

> <EXACT_MASS>
358.189257325

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.62272854632946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(2-{3-[(2S)-2-methoxy-5-oxopyrrolidin-1-yl]propanoyl}phenyl)-2,2-dimethylbut-3-enamide

> <JCHEM_LOGP>
2.991330430333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.02308651144504

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.855142177156244

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8992538015574583

> <JCHEM_POLAR_SURFACE_AREA>
75.71000000000001

> <JCHEM_REFRACTIVITY>
100.8577

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-(2-{3-[(2S)-2-methoxy-5-oxopyrrolidin-1-yl]propanoyl}phenyl)-2,2-dimethylbut-3-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JAN-23         0                                  
HETATM    1  O   UNK     0      11.804  11.205   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.470  10.435   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.137  11.205   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.367   9.871   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.907  12.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.803  11.975   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.803  13.515   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      10.470   8.895   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      11.804   8.125   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.138   8.895   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.471   8.125   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.471   6.585   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.138   5.815   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.804   6.585   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.470   5.815   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.470   4.275   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.137   3.505   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       9.137   1.965   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      10.382   1.060   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.907  -0.405   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.367  -0.405   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.891   1.060   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.426   1.536   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.282   0.505   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.847   1.536   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.137   6.585   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   19                                                            
CONECT   26   15                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆N₂O₄

Average Mass

358.4380 Da

Monoisotopic Mass

358.18926 Da

IUPAC Name

N-(2-{3-[(2S)-2-methoxy-5-oxopyrrolidin-1-yl]propanoyl}phenyl)-2,2-dimethylbut-3-enamide

Traditional Name

N-(2-{3-[(2S)-2-methoxy-5-oxopyrrolidin-1-yl]propanoyl}phenyl)-2,2-dimethylbut-3-enamide

CAS Registry Number

Not Available

SMILES

CO[C@H]1CCC(=O)N1CCC(=O)C1=CC=CC=C1NC(=O)C(C)(C)C=C

InChI Identifier

InChI=1S/C20H26N2O4/c1-5-20(2,3)19(25)21-15-9-7-6-8-14(15)16(23)12-13-22-17(24)10-11-18(22)26-4/h5-9,18H,1,10-13H2,2-4H3,(H,21,25)/t18-/m0/s1

InChI Key

HOXLTIXGFZABJS-SFHVURJKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-04-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-04-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-04-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-04-23	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-04-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-04-23	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-04-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-04-23	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
brocae MA-231		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Methoxyaniline
Anilide
Aryl alkyl ketone
N-arylamide
Benzoyl
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
N-alkylpyrrolidine
2-pyrrolidone
Pyrrolidone
N-acyl-amine
Monocyclic benzene moiety
Vinylogous amide
Alpha,beta-unsaturated ketone
Tertiary carboxylic acid amide
Pyrrolidine
Enone
Acryloyl-group
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.99	ChemAxon
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	75.71 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	100.86 m³·mol⁻¹	ChemAxon
Polarizability	38.62 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Meng LH, Awakawa T, Li XM, Quan Z, Yang SQ, Wang BG, Abe I: Discovery of (+/-)-Penindolenes Reveals an Unusual Indole Ring Cleavage Pathway Catalyzed by P450 Monooxygenase. Angew Chem Int Ed Engl. 2024 Apr 18:e202403963. doi: 10.1002/anie.202403963. [PubMed:38635317 ]

Showing NP-Card for (±)-Penindolene B (NP0332838)

MOL for NP0332838 ((±)-Penindolene B)

3D MOL for NP0332838 ((±)-Penindolene B)

3D SDF for NP0332838 ((±)-Penindolene B)

3D-SDF for NP0332838 ((±)-Penindolene B)

PDB for NP0332838 ((±)-Penindolene B)

3D PDB for NP0332838 ((±)-Penindolene B)

SMILES for NP0332838 ((±)-Penindolene B)

INCHI for NP0332838 ((±)-Penindolene B)

Structure for NP0332838 ((±)-Penindolene B)

3D Structure for NP0332838 ((±)-Penindolene B)