NP-MRD: Showing NP-Card for Tetraphyllin B (NP0045489)

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Record Information

Version

2.0

Created at

2022-03-17 19:20:50 UTC

Updated at

2022-03-17 19:20:50 UTC

NP-MRD ID

NP0045489

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tetraphyllin B

Description

Tetraphyllin B, also known as barterin, belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Tetraphyllin B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Tetraphyllin B has been detected, but not quantified in, papaya. Tetraphyllin B is found in Adenia cissampeloides, Adenia digitata, Adenia volkensii, Androsiphonia adenostegia, Bartera fistulosa, Barteria fistulosa, Carica papaya, Lindackeria dentata, Malesherbia auristipulata, Mathurina penduliflora, Passiflora coriacea Juss. , Passiflora discophora Jorg & Law., Passiflora foetida L. , Passiflora perfoliata, Passiflora tetrandra Banks & Sol.ex.DC., Passiflora tetrandra, Turnera diffusa and Turnera ulmifolia. This could make tetraphyllin b a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061304542D          

 20 21  0  0  0  0            999 V2000
    2.5432    1.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7981    2.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4633    2.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342    5.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5357    3.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182    1.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292    4.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7492    3.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3442    3.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4808    3.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007    3.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1307    3.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9407    4.6216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5592    5.3663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2333    1.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5741    3.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7641    2.4999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8858    2.4827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957    4.6303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7257    3.9029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  5  1  0  0  0  0
 13  5  3  0  0  0  0
 14  4  1  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19  7  1  0  0  0  0
 19 11  1  0  0  0  0
 20 11  1  0  0  0  0
 20 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045489

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2(CC(O)C=C2)C#N)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H17NO7/c13-5-12(2-1-6(15)3-12)20-11-10(18)9(17)8(16)7(4-14)19-11/h1-2,6-11,14-18H,3-4H2

> <INCHI_KEY>
JRCWYCAEAZEYNW-UHFFFAOYSA-N

> <FORMULA>
C12H17NO7

> <MOLECULAR_WEIGHT>
287.2659

> <EXACT_MASS>
287.100501903

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
27.281256687531727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile

> <ALOGPS_LOGP>
-1.96

> <JCHEM_LOGP>
-2.680250793333333

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.187995762787704

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.206697891243529

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9133000556887545

> <JCHEM_POLAR_SURFACE_AREA>
143.4

> <JCHEM_REFRACTIVITY>
64.62599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.747   3.574   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.223   5.039   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.731   5.039   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.371  10.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.733   7.285   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.207   3.574   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.615   8.659   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.399   7.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.643   5.992   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.897   5.976   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.681   7.301   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.977   5.944   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.489   8.627   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      -2.911  10.017   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.302   2.328   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.938   7.350   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.426   4.666   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.653   4.634   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.925   8.643   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.221   7.285   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1   12                                                       
CONECT    3    6   12                                                       
CONECT    4    7   14                                                       
CONECT    5   12   13                                                       
CONECT    6    1    3   15                                                  
CONECT    7    4    8   19                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   19   20                                                  
CONECT   12    2    3    5   20                                             
CONECT   13    5                                                            
CONECT   14    4                                                            
CONECT   15    6                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19    7   11                                                       
CONECT   20   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
(1S,4S)-Tetraphyllin b	HMDB
Barterin	HMDB
TETRAPHYLLIN b: epitetraphyllin b (KCS-2ca)	HMDB

Chemical Formula

C₁₂H₁₇NO₇

Average Mass

287.2659 Da

Monoisotopic Mass

287.10050 Da

IUPAC Name

4-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile

Traditional Name

4-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile

CAS Registry Number

34323-07-4

SMILES

OCC1OC(OC2(CC(O)C=C2)C#N)C(O)C(O)C1O

InChI Identifier

InChI=1S/C12H17NO7/c13-5-12(2-1-6(15)3-12)20-11-10(18)9(17)8(16)7(4-14)19-11/h1-2,6-11,14-18H,3-4H2

InChI Key

JRCWYCAEAZEYNW-UHFFFAOYSA-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
Adenia cissampeloides	LOTUS Database	35616633
Adenia digitata	LOTUS Database	35616633
Adenia volkensii	LOTUS Database	35616633
Androsiphonia adenostegia	LOTUS Database	35616633
Bartera fistulosa	-	KNApSAcK
Barteria fistulosa	Plant	KNApSAcK
Carica papaya	LOTUS Database	35616633
Carica papaya L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lindackeria dentata	LOTUS Database	35616633
Malesherbia auristipulata	LOTUS Database	35616633
Mathurina penduliflora	LOTUS Database	35616633
Passiflora coriacea	Plant	KNApSAcK
Passiflora discophora Jorg & Law.	Plant	KNApSAcK
Passiflora foetida	Plant	KNApSAcK
Passiflora perfoliata	LOTUS Database	35616633
Passiflora tetrandra Banks & Sol.ex.DC.	Plant	KNApSAcK
Tetrapathaea tetrandra	LOTUS Database	35616633
Turnera diffusa	Plant	KNApSAcK
Turnera ulmifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Cyanogenic glycosides

Alternative Parents

Substituents

Cyanogenic glycoside
Hexose monosaccharide
O-glycosyl compound
Monosaccharide
Oxane
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Nitrile
Carbonitrile
Acetal
Primary alcohol
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	ALOGPS
logP	-2.7	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	143.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.63 m³·mol⁻¹	ChemAxon
Polarizability	27.28 Å³	ChemAxon
Number of Rings	2	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

HMDB0029914

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001169

KNApSAcK ID

C00036338

Chemspider ID

103047

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

115164

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tetraphyllin B (NP0045489)

MOL for NP0045489 (Tetraphyllin B)

3D MOL for NP0045489 (Tetraphyllin B)

3D SDF for NP0045489 (Tetraphyllin B)

3D-SDF for NP0045489 (Tetraphyllin B)

PDB for NP0045489 (Tetraphyllin B)

3D PDB for NP0045489 (Tetraphyllin B)

SMILES for NP0045489 (Tetraphyllin B)

INCHI for NP0045489 (Tetraphyllin B)

Structure for NP0045489 (Tetraphyllin B)

3D Structure for NP0045489 (Tetraphyllin B)