NP-MRD: Showing NP-Card for Baconipyrone B (NP0076223)

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Record Information

Version

2.0

Created at

2022-04-28 21:22:41 UTC

Updated at

2022-04-28 21:22:42 UTC

NP-MRD ID

NP0076223

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Baconipyrone B

Description

(1R,2S,3S,4S,6S)-3-ethyl-3-hydroxy-2,4,6-trimethyl-5-oxocyclohexyl (2S,3S,4R,6R)-3-hydroxy-2,4-dimethyl-5-oxo-6-(3,5,6-trimethyl-4-oxo-4H-pyran-2-yl)heptanoate belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Baconipyrone B is found in Siphonaria baconi. Based on a literature review very few articles have been published on (1R,2S,3S,4S,6S)-3-ethyl-3-hydroxy-2,4,6-trimethyl-5-oxocyclohexyl (2S,3S,4R,6R)-3-hydroxy-2,4-dimethyl-5-oxo-6-(3,5,6-trimethyl-4-oxo-4H-pyran-2-yl)heptanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223222D          

 36 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282223222D          

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  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
 12 20  1  0  0  0  0
 10 21  1  1  0  0  0
  7 22  1  6  0  0  0
  6 23  1  1  0  0  0
  5 24  1  6  0  0  0
  1 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  1 30  1  0  0  0  0
 30 31  1  1  0  0  0
 27 32  1  6  0  0  0
 26 33  1  6  0  0  0
 26 34  1  1  0  0  0
 34 35  1  0  0  0  0
 25 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0076223

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@]1(O)[C@@H](C)[C@@H](OC(=O)[C@@H](C)[C@@H](O)[C@@H](C)C(=O)[C@H](C)C2=C(C)C(=O)C(C)=C(C)O2)[C@H](C)C(=O)[C@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O8/c1-11-28(34)18(8)24(32)16(6)26(19(28)9)36-27(33)17(7)23(31)13(3)22(30)15(5)25-14(4)21(29)12(2)20(10)35-25/h13,15-19,23,26,31,34H,11H2,1-10H3/t13-,15-,16+,17-,18+,19-,23-,26-,28+/m0/s1

> <INCHI_KEY>
JNKMSCYJWSFNIT-RIMWVLRUSA-N

> <FORMULA>
C28H42O8

> <MOLECULAR_WEIGHT>
506.636

> <EXACT_MASS>
506.287968312

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
55.457841529220744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,4S,6S)-3-ethyl-3-hydroxy-2,4,6-trimethyl-5-oxocyclohexyl (2S,3S,4R,6R)-3-hydroxy-2,4-dimethyl-5-oxo-6-(3,5,6-trimethyl-4-oxo-4H-pyran-2-yl)heptanoate

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
4.284370637333332

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.929649975094183

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.689094249827544

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1150430194134406

> <JCHEM_POLAR_SURFACE_AREA>
127.2

> <JCHEM_REFRACTIVITY>
136.9239

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,4S,6S)-3-ethyl-3-hydroxy-2,4,6-trimethyl-5-oxocyclohexyl (2S,3S,4R,6R)-3-hydroxy-2,4-dimethyl-5-oxo-6-(3,5,6-trimethyl-4-oxopyran-2-yl)heptanoate

> <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      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -7.484  -9.776   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -8.207  -8.524   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -9.024  -7.218   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.335 -10.780   0.000  0.00  0.00           C+0
CONECT    1    2   25   30                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   24                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   21                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   11                                                       
CONECT   18   16                                                            
CONECT   19   15                                                            
CONECT   20   12                                                            
CONECT   21   10                                                            
CONECT   22    7                                                            
CONECT   23    6                                                            
CONECT   24    5                                                            
CONECT   25    1   26   36                                                  
CONECT   26   25   27   33   34                                             
CONECT   27   26   28   32                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    1   31                                                  
CONECT   31   30                                                            
CONECT   32   27                                                            
CONECT   33   26                                                            
CONECT   34   26   35                                                       
CONECT   35   34                                                            
CONECT   36   25                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,3S,4S,6S)-3-Ethyl-3-hydroxy-2,4,6-trimethyl-5-oxocyclohexyl (2S,3S,4R,6R)-3-hydroxy-2,4-dimethyl-5-oxo-6-(3,5,6-trimethyl-4-oxo-4H-pyran-2-yl)heptanoic acid	Generator

Chemical Formula

C₂₈H₄₂O₈

Average Mass

506.6360 Da

Monoisotopic Mass

506.28797 Da

IUPAC Name

(1R,2S,3S,4S,6S)-3-ethyl-3-hydroxy-2,4,6-trimethyl-5-oxocyclohexyl (2S,3S,4R,6R)-3-hydroxy-2,4-dimethyl-5-oxo-6-(3,5,6-trimethyl-4-oxo-4H-pyran-2-yl)heptanoate

Traditional Name

(1R,2S,3S,4S,6S)-3-ethyl-3-hydroxy-2,4,6-trimethyl-5-oxocyclohexyl (2S,3S,4R,6R)-3-hydroxy-2,4-dimethyl-5-oxo-6-(3,5,6-trimethyl-4-oxopyran-2-yl)heptanoate

CAS Registry Number

Not Available

SMILES

CC[C@]1(O)[C@@H](C)[C@@H](OC(=O)[C@@H](C)[C@@H](O)[C@@H](C)C(=O)[C@H](C)C2=C(C)C(=O)C(C)=C(C)O2)[C@H](C)C(=O)[C@H]1C

InChI Identifier

InChI=1S/C28H42O8/c1-11-28(34)18(8)24(32)16(6)26(19(28)9)36-27(33)17(7)23(31)13(3)22(30)15(5)25-14(4)21(29)12(2)20(10)35-25/h13,15-19,23,26,31,34H,11H2,1-10H3/t13-,15-,16+,17-,18+,19-,23-,26-,28+/m0/s1

InChI Key

JNKMSCYJWSFNIT-RIMWVLRUSA-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
Siphonaria baconi	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Pyranone
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Hydroxy acid
Beta-hydroxy ketone
Heteroaromatic compound
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.96	ALOGPS
logP	4.28	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	127.2 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	136.92 m³·mol⁻¹	ChemAxon
Polarizability	55.46 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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

162987823

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Baconipyrone B (NP0076223)

MOL for NP0076223 (Baconipyrone B)

3D MOL for NP0076223 (Baconipyrone B)

3D SDF for NP0076223 (Baconipyrone B)

3D-SDF for NP0076223 (Baconipyrone B)

PDB for NP0076223 (Baconipyrone B)

3D PDB for NP0076223 (Baconipyrone B)

SMILES for NP0076223 (Baconipyrone B)

INCHI for NP0076223 (Baconipyrone B)

Structure for NP0076223 (Baconipyrone B)

3D Structure for NP0076223 (Baconipyrone B)