NP-MRD: Showing NP-Card for 2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate (NP0173903)

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Record Information

Version

2.0

Created at

2022-09-03 11:05:52 UTC

Updated at

2022-09-03 11:05:52 UTC

NP-MRD ID

NP0173903

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate

Description

2-(Acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. 2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate is found in Alvaradoa haitiensis. 2-(Acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171513492D          

 38 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171513492D          

 38 41  0  0  0  0            999 V2000
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 21 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  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 19 37  1  0  0  0  0
 30 37  1  0  0  0  0
  2 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0173903

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC(=O)OC1C(O)C(OC(C)=O)OC(C1O)C1(O)C2=CC=CC(O)=C2C(=O)C2=C(O)C=C(C)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O11/c1-11(2)8-18(31)37-24-22(33)25(38-26(23(24)34)36-13(4)28)27(35)14-6-5-7-16(29)19(14)21(32)20-15(27)9-12(3)10-17(20)30/h5-10,22-26,29-30,33-35H,1-4H3

> <INCHI_KEY>
CWTBVTWONZDFAF-UHFFFAOYSA-N

> <FORMULA>
C27H28O11

> <MOLECULAR_WEIGHT>
528.51

> <EXACT_MASS>
528.163161722

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
51.970282774574265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
3.555494589666666

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.954010491362325

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.30186244368002

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6822339198165537

> <JCHEM_POLAR_SURFACE_AREA>
180.05

> <JCHEM_REFRACTIVITY>
131.3361

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-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       5.854  12.817   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.380  11.370   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.391  10.191   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.917   8.743   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.434   8.476   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.927   7.564   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.454   6.117   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.971   5.849   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.961   7.029   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.497   4.402   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.014   4.135   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.004   5.314   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.477   6.761   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.521   5.047   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.508   3.222   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.991   3.490   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.464   4.937   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.948   5.204   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.011   3.490   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.897  11.103   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16    7   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20   21   37                                             
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   21   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   37                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   19   30                                                  
CONECT   38    2                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
2-(Acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₇H₂₈O₁₁

Average Mass

528.5100 Da

Monoisotopic Mass

528.16316 Da

IUPAC Name

2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate

Traditional Name

2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC(C)=CC(=O)OC1C(O)C(OC(C)=O)OC(C1O)C1(O)C2=CC=CC(O)=C2C(=O)C2=C(O)C=C(C)C=C12

InChI Identifier

InChI=1S/C27H28O11/c1-11(2)8-18(31)37-24-22(33)25(38-26(23(24)34)36-13(4)28)27(35)14-6-5-7-16(29)19(14)21(32)20-15(27)9-12(3)10-17(20)30/h5-10,22-26,29-30,33-35H,1-4H3

InChI Key

CWTBVTWONZDFAF-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
Alvaradoa haitiensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Not Available

Direct Parent

Anthracenes

Alternative Parents

Substituents

Anthracene
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Fatty acyl
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Ketone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Acetal
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen 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	1.66	ALOGPS
logP	3.56	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.05 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	131.34 m³·mol⁻¹	ChemAxon
Polarizability	51.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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 2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate (NP0173903)

MOL for NP0173903 (2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate)

3D MOL for NP0173903 (2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate)

3D SDF for NP0173903 (2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate)

3D-SDF for NP0173903 (2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate)

PDB for NP0173903 (2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate)

3D PDB for NP0173903 (2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate)

SMILES for NP0173903 (2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate)

INCHI for NP0173903 (2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate)

Structure for NP0173903 (2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate)

3D Structure for NP0173903 (2-(acetyloxy)-3,5-dihydroxy-6-(4,5,9-trihydroxy-2-methyl-10-oxoanthracen-9-yl)oxan-4-yl 3-methylbut-2-enoate)