NP-MRD: Showing NP-Card for (2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate (NP0286328)

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Record Information

Version

2.0

Created at

2022-09-09 14:51:17 UTC

Updated at

2022-09-09 14:51:17 UTC

NP-MRD ID

NP0286328

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate

Description

ALVARADOIN B belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. (2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate is found in Alvaradoa jamaicensis. Based on a literature review very few articles have been published on ALVARADOIN B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092216512D          

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M  END

     RDKit          3D

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  Mrv1652309092216512D          

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 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 19 27  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  1  0  0  0
 10 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0286328

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C3=C(O)C=C(C)C=C3[C@@H]([C@H]3OC[C@H](OC(C)=O)[C@H](OC(=O)C=C(C)C)[C@H]3O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O10/c1-12(2)6-21(32)38-27-20(37-14(4)29)11-36-28(26(27)34)22-16-7-13(3)8-18(30)23(16)25(33)24-17(22)9-15(35-5)10-19(24)31/h6-10,20,22,26-28,30-31,34H,11H2,1-5H3/t20-,22+,26+,27-,28+/m0/s1

> <INCHI_KEY>
LARBGQKKKKPZPS-MNBWDCGASA-N

> <FORMULA>
C28H30O10

> <MOLECULAR_WEIGHT>
526.538

> <EXACT_MASS>
526.183897166

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.58666365396139

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5S)-5-(acetyloxy)-2-[(9R)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9,10-dihydroanthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate

> <JCHEM_LOGP>
4.670297986

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.062596530931234

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.396292125410104

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6409911299326643

> <JCHEM_POLAR_SURFACE_AREA>
148.82000000000002

> <JCHEM_REFRACTIVITY>
135.4253

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5S)-5-(acetyloxy)-2-[(9R)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9H-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335   1.540   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  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -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       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   37                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   29                                                  
CONECT   11   10   12   27                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   19   11   28                                                  
CONECT   28   27                                                            
CONECT   29   10   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29   37                                                  
CONECT   37   36    7   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₀O₁₀

Average Mass

526.5380 Da

Monoisotopic Mass

526.18390 Da

IUPAC Name

(2R,3S,4R,5S)-5-(acetyloxy)-2-[(9R)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9,10-dihydroanthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate

Traditional Name

(2R,3S,4R,5S)-5-(acetyloxy)-2-[(9R)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9H-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C3=C(O)C=C(C)C=C3[C@@H]([C@H]3OC[C@H](OC(C)=O)[C@H](OC(=O)C=C(C)C)[C@H]3O)C2=C1

InChI Identifier

InChI=1S/C28H30O10/c1-12(2)6-21(32)38-27-20(37-14(4)29)11-36-28(26(27)34)22-16-7-13(3)8-18(30)23(16)25(33)24-17(22)9-15(35-5)10-19(24)31/h6-10,20,22,26-28,30-31,34H,11H2,1-5H3/t20-,22+,26+,27-,28+/m0/s1

InChI Key

LARBGQKKKKPZPS-MNBWDCGASA-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 jamaicensis	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
Anisole
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Dicarboxylic acid or derivatives
Oxane
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Vinylogous acid
Secondary alcohol
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Carboxylic acid derivative
Dialkyl ether
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	4.67	ChemAxon
pKa (Strongest Acidic)	8.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	135.43 m³·mol⁻¹	ChemAxon
Polarizability	53.59 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

C00049106

Chemspider ID

23326439

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44558973

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate (NP0286328)

MOL for NP0286328 ((2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate)

3D MOL for NP0286328 ((2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate)

3D SDF for NP0286328 ((2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate)

3D-SDF for NP0286328 ((2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate)

PDB for NP0286328 ((2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate)

3D PDB for NP0286328 ((2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate)

SMILES for NP0286328 ((2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate)

INCHI for NP0286328 ((2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate)

Structure for NP0286328 ((2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate)

3D Structure for NP0286328 ((2r,3s,4r,5s)-5-(acetyloxy)-2-[(9r)-4,5-dihydroxy-2-methoxy-7-methyl-10-oxo-9h-anthracen-9-yl]-3-hydroxyoxan-4-yl 3-methylbut-2-enoate)