NP-MRD: Showing NP-Card for Koninginin B (NP0066432)

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Record Information

Version

2.0

Created at

2022-04-28 10:41:21 UTC

Updated at

2022-04-28 10:41:21 UTC

NP-MRD ID

NP0066432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Koninginin B

Description

Koninginin B belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Koninginin B is found in Diffenbachia sp. ATCC 46314 and Trichoderma koningii. Koninginin B was first documented in 2011 (PMID: 21301186). Based on a literature review a small amount of articles have been published on koninginin B (PMID: 31785858) (PMID: 29685076).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 47  0  0  0  0  0  0  0  0999 V2000
    6.3126   -0.2687    0.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9817    0.4897   -0.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7127   -0.1350   -1.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6378    0.0203   -0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3177   -0.5569   -0.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3303   -0.3377    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0362   -0.8863   -0.1482 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1352   -2.2669   -0.3891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9323   -0.6965    1.0500 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1041    0.7521    1.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8104    1.4437    0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1324    0.7763    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2523   -0.5046    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2067   -1.2719    0.8578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5933   -1.1178    0.1923 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6906   -2.3496    0.8368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6095   -0.1280    0.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6858    1.0387   -0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2733    1.5060   -0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0642    2.5784   -1.0540 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1158   -1.3414    0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7190    0.1190    1.1984 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3850   -0.0656    0.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8244    0.4004   -1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7599    1.5458   -0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4218    0.3884   -2.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8509   -1.2069   -1.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4566    1.0995   -0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9396   -0.5336    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3799   -1.6521   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9311   -0.0733   -1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3272    0.7298    0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6764   -0.8953    1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4229   -0.4615   -1.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8494   -2.6275    0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4369   -1.2138    1.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1858    1.2634    1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8120    0.8138    2.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2806    1.3558   -0.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9297    2.5275    0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8276   -1.2094   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6437   -3.0374    0.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2063    0.2912    1.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5939   -0.5962    0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2340    1.8607    0.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1006    0.7216   -1.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 14  9  1  0
 19 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  6
  8 35  1  0
  9 36  1  1
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 15 41  1  6
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
M  END


  Mrv1652304282212412D          

 20 21  0  0  1  0            999 V2000
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 10 13  1  1  0  0  0
 13 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
 13 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0066432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC[C@@H](O)[C@H]1CCC2=C(O1)[C@@H](O)CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O4/c1-2-3-4-5-6-13(18)15-10-7-11-12(17)8-9-14(19)16(11)20-15/h13-15,18-19H,2-10H2,1H3/t13-,14+,15-/m1/s1

> <INCHI_KEY>
INHVGPIPHZJQOP-QLFBSQMISA-N

> <FORMULA>
C16H26O4

> <MOLECULAR_WEIGHT>
282.38

> <EXACT_MASS>
282.183109317

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
31.870526941500735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,8S)-8-hydroxy-2-[(1R)-1-hydroxyheptyl]-3,4,5,6,7,8-hexahydro-2H-1-benzopyran-5-one

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
2.1508105866666662

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.352369816574601

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.692284678927134

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1563297075609285

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
78.0355

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,8S)-8-hydroxy-2-[(1R)-1-hydroxyheptyl]-2,3,4,6,7,8-hexahydro-1-benzopyran-5-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      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    5                                                       
CONECT   13   10   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   13                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₆O₄

Average Mass

282.3800 Da

Monoisotopic Mass

282.18311 Da

IUPAC Name

(2R,8S)-8-hydroxy-2-[(1R)-1-hydroxyheptyl]-3,4,5,6,7,8-hexahydro-2H-1-benzopyran-5-one

Traditional Name

(2R,8S)-8-hydroxy-2-[(1R)-1-hydroxyheptyl]-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one

CAS Registry Number

Not Available

SMILES

CCCCCC[C@@H](O)[C@H]1CCC2=C(O1)[C@@H](O)CCC2=O

InChI Identifier

InChI=1S/C16H26O4/c1-2-3-4-5-6-13(18)15-10-7-11-12(17)8-9-14(19)16(11)20-15/h13-15,18-19H,2-10H2,1H3/t13-,14+,15-/m1/s1

InChI Key

INHVGPIPHZJQOP-QLFBSQMISA-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
Diffenbachia sp. ATCC 46314	-	KNApSAcK
Trichoderma koningii	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Fatty alcohol
Cyclohexenone
Fatty acyl
Vinylogous ester
Secondary alcohol
Ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.93	ALOGPS
logP	2.15	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.69	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	78.04 m³·mol⁻¹	ChemAxon
Polarizability	31.87 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

C00023952

Chemspider ID

23327343

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559759

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shi XS, Li HL, Li XM, Wang DJ, Li X, Meng LH, Zhou XW, Wang BG: Highly oxygenated polyketides produced by Trichoderma koningiopsis QA-3, an endophytic fungus obtained from the fresh roots of the medicinal plant Artemisia argyi. Bioorg Chem. 2020 Jan;94:103448. doi: 10.1016/j.bioorg.2019.103448. Epub 2019 Nov 21. [PubMed:31785858 ]
Chen L, Wu GW, Liu D, Zhuang WY, Yin WB: Trichodermatides E and F from fungus Trichoderma applanatum. J Asian Nat Prod Res. 2019 Jul;21(7):659-665. doi: 10.1080/10286020.2018.1465051. Epub 2018 Apr 23. [PubMed:29685076 ]
Kang D, Kim J, Choi JN, Liu KH, Lee CH: Chemotaxonomy of Trichoderma spp. Using mass spectrometry-based metabolite profiling. J Microbiol Biotechnol. 2011 Jan;21(1):5-13. doi: 10.4014/jmb.1008.08018. [PubMed:21301186 ]

Showing NP-Card for Koninginin B (NP0066432)

MOL for NP0066432 (Koninginin B)

3D MOL for NP0066432 (Koninginin B)

3D SDF for NP0066432 (Koninginin B)

3D-SDF for NP0066432 (Koninginin B)

PDB for NP0066432 (Koninginin B)

3D PDB for NP0066432 (Koninginin B)

SMILES for NP0066432 (Koninginin B)

INCHI for NP0066432 (Koninginin B)

Structure for NP0066432 (Koninginin B)

3D Structure for NP0066432 (Koninginin B)