NP-MRD: Showing NP-Card for (-)-Alvaradoin C (NP0082281)

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Record Information

Version

2.0

Created at

2022-04-29 03:19:31 UTC

Updated at

2022-04-29 03:19:31 UTC

NP-MRD ID

NP0082281

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Alvaradoin C

Description

ALVARADOIN C belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. (-)-Alvaradoin C is found in Alvaradoa jamaicensis. Based on a literature review very few articles have been published on ALVARADOIN C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205192D          

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    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


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 22 24  1  0  0  0  0
  9 25  1  1  0  0  0
  7 26  1  1  0  0  0
  6 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
 28 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
  1 37  1  0  0  0  0
 36 38  1  0  0  0  0
 34 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0082281

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(C)C=C1O)[C@]2(O)[C@@H]1OC[C@@H](OC(C)=O)[C@@H](OC(=O)C=C(C)C)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O11/c1-12(2)6-21(32)39-26-20(38-14(4)29)11-37-27(25(26)34)28(35)16-7-13(3)8-18(30)22(16)24(33)23-17(28)9-15(36-5)10-19(23)31/h6-10,20,25-27,30-31,34-35H,11H2,1-5H3/t20-,25+,26-,27-,28-/m1/s1

> <INCHI_KEY>
OLGFJNYTTKMULR-JALBJSGRSA-N

> <FORMULA>
C28H30O11

> <MOLECULAR_WEIGHT>
542.537

> <EXACT_MASS>
542.178811786

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.84846297124864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
3.7620472656666664

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.918593204211854

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.251038792800081

> <JCHEM_PKA_STRONGEST_BASIC>
-3.678070481498537

> <JCHEM_POLAR_SURFACE_AREA>
169.04999999999998

> <JCHEM_REFRACTIVITY>
136.76940000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R)-5-(acetyloxy)-3-hydroxy-2-[(9R)-4,5,9-trihydroxy-2-methoxy-7-methyl-10-oxoanthracen-9-yl]oxan-4-yl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.278  -2.130   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.094  -3.436   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.371  -4.795   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.832  -4.849   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.016  -3.543   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.739  -2.183   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.109  -6.209   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.925  -7.515   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.464  -7.461   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.202  -8.875   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.187  -6.101   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.726  -6.048   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.449  -4.688   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.542  -7.354   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.819  -8.713   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.635 -10.019   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.280  -8.767   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.633  -3.382   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.724  -2.130   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    7   37                                                  
CONECT    2    1    3   34                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   30                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    1    8   26                                             
CONECT    8    7    9   13                                                  
CONECT    9    8   10   25                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   10   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    9                                                            
CONECT   26    7                                                            
CONECT   27    6   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29    5   31                                                  
CONECT   31   30                                                            
CONECT   32   28   33                                                       
CONECT   33   32                                                            
CONECT   34    2   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36    1                                                       
CONECT   38   36                                                            
CONECT   39   34                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₀O₁₁

Average Mass

542.5370 Da

Monoisotopic Mass

542.17881 Da

IUPAC Name

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

Traditional Name

(2R,3S,4S,5R)-5-(acetyloxy)-3-hydroxy-2-[(9R)-4,5,9-trihydroxy-2-methoxy-7-methyl-10-oxoanthracen-9-yl]oxan-4-yl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(C)C=C1O)[C@]2(O)[C@@H]1OC[C@@H](OC(C)=O)[C@@H](OC(=O)C=C(C)C)[C@@H]1O

InChI Identifier

InChI=1S/C28H30O11/c1-12(2)6-21(32)39-26-20(38-14(4)29)11-37-27(25(26)34)28(35)16-7-13(3)8-18(30)22(16)24(33)23-17(28)9-15(36-5)10-19(23)31/h6-10,20,25-27,30-31,34-35H,11H2,1-5H3/t20-,25+,26-,27-,28-/m1/s1

InChI Key

OLGFJNYTTKMULR-JALBJSGRSA-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
Alvaradoa jamaicensis	Plant	KNApSAcK

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
Oxane
Fatty acyl
Dicarboxylic acid or derivatives
Vinylogous acid
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Organoheterocyclic compound
Ether
Polyol
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	2.17	ALOGPS
logP	3.76	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.25	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	169.05 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	136.77 m³·mol⁻¹	ChemAxon
Polarizability	53.85 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

C00049107

Chemspider ID

8849400

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10674050

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Alvaradoin C (NP0082281)

MOL for NP0082281 ((-)-Alvaradoin C)

3D MOL for NP0082281 ((-)-Alvaradoin C)

3D SDF for NP0082281 ((-)-Alvaradoin C)

3D-SDF for NP0082281 ((-)-Alvaradoin C)

PDB for NP0082281 ((-)-Alvaradoin C)

3D PDB for NP0082281 ((-)-Alvaradoin C)

SMILES for NP0082281 ((-)-Alvaradoin C)

INCHI for NP0082281 ((-)-Alvaradoin C)

Structure for NP0082281 ((-)-Alvaradoin C)

3D Structure for NP0082281 ((-)-Alvaradoin C)