NP-MRD: Showing NP-Card for (2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate (NP0325120)

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Record Information

Version

2.0

Created at

2022-09-12 05:38:11 UTC

Updated at

2022-09-12 05:38:12 UTC

NP-MRD ID

NP0325120

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate

Description

(2S,3R,4R,5R,6S)-2-(acetyloxy)-6-[(9R)-4,5-dihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl]-3,5-dihydroxyoxan-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. (2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate is found in Alvaradoa haitiensis. Based on a literature review very few articles have been published on (2S,3R,4R,5R,6S)-2-(acetyloxy)-6-[(9R)-4,5-dihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122207382D          

 37 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309122207382D          

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 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 28 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0325120

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC(=O)O[C@H]1[C@@H](O)[C@H](OC(C)=O)O[C@H]([C@H]1O)[C@@H]1C2=CC=CC(O)=C2C(=O)C2=C(O)C=C(C)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O10/c1-11(2)8-18(31)36-26-23(33)25(37-27(24(26)34)35-13(4)28)19-14-6-5-7-16(29)20(14)22(32)21-15(19)9-12(3)10-17(21)30/h5-10,19,23-27,29-30,33-34H,1-4H3/t19-,23-,24-,25+,26-,27-/m1/s1

> <INCHI_KEY>
NVWRUTJMHZBGQX-HZSNDBBCSA-N

> <FORMULA>
C27H28O10

> <MOLECULAR_WEIGHT>
512.511

> <EXACT_MASS>
512.168247102

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
51.35252578651742

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6S)-2-(acetyloxy)-6-[(9R)-4,5-dihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate

> <JCHEM_LOGP>
4.463745309999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.09607498338119

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.44396417381296

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6451453411767867

> <JCHEM_POLAR_SURFACE_AREA>
159.82000000000002

> <JCHEM_REFRACTIVITY>
129.99200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6S)-2-(acetyloxy)-6-[(9R)-4,5-dihydroxy-2-methyl-10-oxo-9H-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667   6.160   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       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.000   9.240   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.000  10.780   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9   25                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18    8                                                  
CONECT   26    7   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   28    5   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4R,5R,6S)-2-(Acetyloxy)-6-[(9R)-4,5-dihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₇H₂₈O₁₀

Average Mass

512.5110 Da

Monoisotopic Mass

512.16825 Da

IUPAC Name

(2S,3R,4R,5R,6S)-2-(acetyloxy)-6-[(9R)-4,5-dihydroxy-2-methyl-10-oxo-9,10-dihydroanthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate

Traditional Name

(2S,3R,4R,5R,6S)-2-(acetyloxy)-6-[(9R)-4,5-dihydroxy-2-methyl-10-oxo-9H-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC(C)=CC(=O)O[C@H]1[C@@H](O)[C@H](OC(C)=O)O[C@H]([C@H]1O)[C@@H]1C2=CC=CC(O)=C2C(=O)C2=C(O)C=C(C)C=C12

InChI Identifier

InChI=1S/C27H28O10/c1-11(2)8-18(31)36-26-23(33)25(37-27(24(26)34)35-13(4)28)19-14-6-5-7-16(29)20(14)22(32)21-15(19)9-12(3)10-17(21)30/h5-10,19,23-27,29-30,33-34H,1-4H3/t19-,23-,24-,25+,26-,27-/m1/s1

InChI Key

NVWRUTJMHZBGQX-HZSNDBBCSA-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
Fatty acyl
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	4.46	ChemAxon
pKa (Strongest Acidic)	8.44	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	159.82 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	129.99 m³·mol⁻¹	ChemAxon
Polarizability	51.35 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

163074146

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate (NP0325120)

MOL for NP0325120 ((2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate)

3D MOL for NP0325120 ((2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate)

3D SDF for NP0325120 ((2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate)

3D-SDF for NP0325120 ((2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate)

PDB for NP0325120 ((2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate)

3D PDB for NP0325120 ((2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate)

SMILES for NP0325120 ((2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate)

INCHI for NP0325120 ((2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate)

Structure for NP0325120 ((2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate)

3D Structure for NP0325120 ((2s,3r,4r,5r,6s)-2-(acetyloxy)-6-[(9r)-4,5-dihydroxy-2-methyl-10-oxo-9h-anthracen-9-yl]-3,5-dihydroxyoxan-4-yl 3-methylbut-2-enoate)