NP-MRD: Showing NP-Card for {3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate (NP0280685)

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Record Information

Version

1.0

Created at

2022-09-09 06:36:54 UTC

Updated at

2022-09-09 06:36:54 UTC

NP-MRD ID

NP0280685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate

Description

{3,4,5-Trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. {3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate is found in Andrographis alata. {3,4,5-Trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171501292D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171501292D          

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 24 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
 30 31  2  0  0  0  0
 31 32  1  4  0  0  0
 25 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 23 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0280685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=C(O)C=CC=C1OC1OC(COC(=O)C=CC)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O12/c1-3-5-20(30)35-11-19-23(31)24(32)25(33)26(38-19)37-16-7-4-6-13(27)22(16)18-10-15(29)21-14(28)8-12(34-2)9-17(21)36-18/h3-10,19,23-28,31-33H,11H2,1-2H3

> <INCHI_KEY>
YVMKWKJABXKOSO-UHFFFAOYSA-N

> <FORMULA>
C26H26O12

> <MOLECULAR_WEIGHT>
530.482

> <EXACT_MASS>
530.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
50.486776943153586

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
2.0983365199999984

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.357683727490807

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.317515462785674

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649110293434476

> <JCHEM_POLAR_SURFACE_AREA>
181.44

> <JCHEM_REFRACTIVITY>
130.9942

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334  -6.930   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       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13    3                                                       
CONECT   15   11   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   25   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   23   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
{3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoic acid	Generator

Chemical Formula

C₂₆H₂₆O₁₂

Average Mass

530.4820 Da

Monoisotopic Mass

530.14243 Da

IUPAC Name

{3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate

Traditional Name

{3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=C(O)C=CC=C1OC1OC(COC(=O)C=CC)C(O)C(O)C1O

InChI Identifier

InChI=1S/C26H26O12/c1-3-5-20(30)35-11-19-23(31)24(32)25(33)26(38-19)37-16-7-4-6-13(27)22(16)18-10-15(29)21-14(28)8-12(34-2)9-17(21)36-18/h3-10,19,23-28,31-33H,11H2,1-2H3

InChI Key

YVMKWKJABXKOSO-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Andrographis alata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Trichothecenes

Alternative Parents

Substituents

Trichothecene skeleton
Cyclohexenone
Oxepane
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Ether
Oxirane
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	2.2	ALOGPS
logP	2.1	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.32	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	181.44 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.99 m³·mol⁻¹	ChemAxon
Polarizability	50.49 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

LOTUS database [Link]

Showing NP-Card for {3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate (NP0280685)

MOL for NP0280685 ({3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate)

3D MOL for NP0280685 ({3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate)

3D SDF for NP0280685 ({3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate)

3D-SDF for NP0280685 ({3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate)

PDB for NP0280685 ({3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate)

3D PDB for NP0280685 ({3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate)

SMILES for NP0280685 ({3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate)

INCHI for NP0280685 ({3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate)

Structure for NP0280685 ({3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate)

3D Structure for NP0280685 ({3,4,5-trihydroxy-6-[3-hydroxy-2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]oxan-2-yl}methyl but-2-enoate)