NP-MRD: Showing NP-Card for Penicilloneine B (NP0332639)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-03-15 03:45:08 UTC

Updated at

2024-11-01 01:39:20 UTC

NP-MRD ID

NP0332639

Natural Product DOI

https://doi.org/10.57994/1899

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Penicilloneine B

Description

Penicilloneine B belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review very few articles have been published on Penicilloneine B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03152403452D          

 30 33  0  0  1  0            999 V2000
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0513   -5.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  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
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  2  0  0  0  0
  8 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
  5 27  1  0  0  0  0
 28 27  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  6  0  0  0
  4 30  2  0  0  0  0
M  END


  Mrv2104 03152403452D          

 30 33  0  0  1  0            999 V2000
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0513   -5.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  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
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  2  0  0  0  0
  8 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
  5 27  1  0  0  0  0
 28 27  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  6  0  0  0
  4 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332639

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1OC(=O)C2=C(O)C(CC3=C(O)C4=CC=CC=C4N(C)C3=O)=C(O)C(C)=C2[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C23H23NO6/c1-10-12(3)30-23(29)18-17(10)11(2)19(25)14(21(18)27)9-15-20(26)13-7-5-6-8-16(13)24(4)22(15)28/h5-8,10,12,25-27H,9H2,1-4H3/t10-,12-/m1/s1

> <INCHI_KEY>
KYDVGTQRWHLYEI-ZYHUDNBSSA-N

> <FORMULA>
C23H23NO6

> <MOLECULAR_WEIGHT>
409.438

> <EXACT_MASS>
409.152537465

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
42.41314977423154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(3R,4S)-6,8-dihydroxy-3,4,5-trimethyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]methyl}-4-hydroxy-1-methyl-1,2-dihydroquinolin-2-one

> <JCHEM_LOGP>
3.8627887056666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.650450988458584

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.761945474553562

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3836776285963057

> <JCHEM_POLAR_SURFACE_AREA>
107.30000000000001

> <JCHEM_REFRACTIVITY>
112.56879999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(3R,4S)-6,8-dihydroxy-3,4,5-trimethyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl]methyl}-4-hydroxy-1-methylquinolin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAR-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAR-24         0                                  
HETATM    1  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      14.670 -10.010   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.296 -10.647   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   30                                                  
CONECT    5    4    6   27                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   23                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   10   22                                                  
CONECT   22   21                                                            
CONECT   23    8   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    5   28                                                  
CONECT   28   27    2   29                                                  
CONECT   29   28                                                            
CONECT   30    4                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₃NO₆

Average Mass

409.4380 Da

Monoisotopic Mass

409.15254 Da

IUPAC Name

3-{[(3R,4S)-6,8-dihydroxy-3,4,5-trimethyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]methyl}-4-hydroxy-1-methyl-1,2-dihydroquinolin-2-one

Traditional Name

3-{[(3R,4S)-6,8-dihydroxy-3,4,5-trimethyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl]methyl}-4-hydroxy-1-methylquinolin-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1OC(=O)C2=C(O)C(CC3=C(O)C4=CC=CC=C4N(C)C3=O)=C(O)C(C)=C2[C@@H]1C

InChI Identifier

InChI=1S/C23H23NO6/c1-10-12(3)30-23(29)18-17(10)11(2)19(25)14(21(18)27)9-15-20(26)13-7-5-6-8-16(13)24(4)22(15)28/h5-8,10,12,25-27H,9H2,1-4H3/t10-,12-/m1/s1

InChI Key

KYDVGTQRWHLYEI-ZYHUDNBSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	20212110040@stu.gzucm.edu.cn	Guangzhou University of Chinese Medicine	Fan Hao	2024-03-21	View Spectrum
1D_ NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	20212110040@stu.gzucm.edu.cn	Guangzhou University of Chinese Medicine	Fan Hao	2024-03-21	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	20212110040@stu.gzucm.edu.cn	Guangzhou University of Chinese Medicine	Fan Hao	2024-03-21	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	20212110040@stu.gzucm.edu.cn	Guangzhou University of Chinese Medicine	Fan Hao	2024-03-21	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	20212110040@stu.gzucm.edu.cn	Guangzhou University of Chinese Medicine	Fan Hao	2024-03-21	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	20212110040@stu.gzucm.edu.cn	Guangzhou University of Chinese Medicine	Fan Hao	2024-03-21	View Spectrum
1D_ NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	20212110040@stu.gzucm.edu.cn	Guangzhou University of Chinese Medicine	Fan Hao	2024-03-21	View Spectrum
1D_ NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	20212110040@stu.gzucm.edu.cn	Guangzhou University of Chinese Medicine	Fan Hao	2024-03-21	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.162470988, CDCl₃, simulated)	20212110040@stu.gzucm.edu.cn	Guangzhou University of Chinese Medicine	Fan Hao	2024-03-15	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Farsesane sesquiterpenoid
Sesquiterpenoid
2-benzopyran
Quinoline
Isochromane
Benzopyran
Polyhalopyridine
Methylpyridine
Hydroxypyridine
Delta_valerolactone
Fatty acid ester
Delta valerolactone
Fatty acyl
Benzenoid
Pyridine
Oxane
N-acyl-amine
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary carboxylic acid amide
Lactone
Lactam
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	3.86	ChemAxon
pKa (Strongest Acidic)	6.76	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	107.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	112.57 m³·mol⁻¹	ChemAxon
Polarizability	42.41 Å³	ChemAxon
Number of Rings	4	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

Showing NP-Card for Penicilloneine B (NP0332639)

MOL for NP0332639 (Penicilloneine B)

3D MOL for NP0332639 (Penicilloneine B)

3D SDF for NP0332639 (Penicilloneine B)

3D-SDF for NP0332639 (Penicilloneine B)

PDB for NP0332639 (Penicilloneine B)

3D PDB for NP0332639 (Penicilloneine B)

SMILES for NP0332639 (Penicilloneine B)

INCHI for NP0332639 (Penicilloneine B)

Structure for NP0332639 (Penicilloneine B)

3D Structure for NP0332639 (Penicilloneine B)