NP-MRD: Showing NP-Card for (-)-Aglaroxin A (NP0077873)

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Record Information

Version

2.0

Created at

2022-04-28 23:01:19 UTC

Updated at

2022-04-28 23:01:19 UTC

NP-MRD ID

NP0077873

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Aglaroxin A

Description

Aglaroxin A belongs to the class of organic compounds known as flavaglines. These are heterocyclic compounds with a structure characterized by a cyclopenta[b]benzofuran skeleton. (-)-Aglaroxin A is found in Aglaia edulis , Aglaia elaeagnoidea and Aglaia oligophylla . Based on a literature review very few articles have been published on aglaroxin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201012D          

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M  END

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  Mrv1652304292201012D          

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 32 33  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
  1 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077873

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)[C@@]12OC3=CC4=C(OCO4)C(OC)=C3[C@]1(O)[C@H](O)[C@@H]([C@H]2C1=CC=CC=C1)C(=O)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H29NO8/c1-30(2)27(32)21-22(16-8-6-5-7-9-16)29(17-10-12-18(34-3)13-11-17)28(33,26(21)31)23-19(38-29)14-20-24(25(23)35-4)37-15-36-20/h5-14,21-22,26,31,33H,15H2,1-4H3/t21-,22-,26-,28+,29+/m1/s1

> <INCHI_KEY>
VBEWJSMISIWDQM-NPWWZGLVSA-N

> <FORMULA>
C29H29NO8

> <MOLECULAR_WEIGHT>
519.55

> <EXACT_MASS>
519.189316898

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
54.00737105964993

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10S,11R,12R,13S,14R)-10,11-dihydroxy-8-methoxy-14-(4-methoxyphenyl)-N,N-dimethyl-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0^{3,7}.0^{10,14}]pentadeca-1,3(7),8-triene-12-carboxamide

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
2.169436275333333

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.054504276197914

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.579488205771192

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6800718178044884

> <JCHEM_POLAR_SURFACE_AREA>
106.92000000000002

> <JCHEM_REFRACTIVITY>
135.5652

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10S,11R,12R,13S,14R)-10,11-dihydroxy-8-methoxy-14-(4-methoxyphenyl)-N,N-dimethyl-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0^{3,7}.0^{10,14}]pentadeca-1,3(7),8-triene-12-carboxamide

> <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       8.033   5.907   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.743   4.394   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.288   3.889   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.123   4.896   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.413   6.409   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.868   6.914   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.064   7.152   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.941   6.098   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.595   4.704   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.472   3.651   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.123   4.394   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.413   5.907   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.064   6.650   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.254   5.853   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.603   6.596   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.634   8.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.316   8.932   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.033   8.189   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.271   3.740   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.535   4.619   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      -0.401   2.205   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       0.863   1.325   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.795   1.550   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.664   2.123   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.250   3.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.286   7.492   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.752   7.622   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.097   9.016   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.977  10.280   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.512  10.150   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.166   8.756   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.323  11.674   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.203  12.938   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.999   2.376   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.164   1.369   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.092   3.651   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.216   4.704   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.561   6.098   0.000  0.00  0.00           O+0
CONECT    1    2    6   38                                                  
CONECT    2    1    3   36                                                  
CONECT    3    2    4   34                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12   26                                             
CONECT    9    8    4   10   25                                             
CONECT   10    9   11   24                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11    8   13                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   11   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   10                                                            
CONECT   25    9                                                            
CONECT   26    8   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   29   33                                                       
CONECT   33   32                                                            
CONECT   34    3   35                                                       
CONECT   35   34                                                            
CONECT   36    2   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37    1                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₂₉NO₈

Average Mass

519.5500 Da

Monoisotopic Mass

519.18932 Da

IUPAC Name

(10S,11R,12R,13S,14R)-10,11-dihydroxy-8-methoxy-14-(4-methoxyphenyl)-N,N-dimethyl-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0^{3,7}.0^{10,14}]pentadeca-1,3(7),8-triene-12-carboxamide

Traditional Name

(10S,11R,12R,13S,14R)-10,11-dihydroxy-8-methoxy-14-(4-methoxyphenyl)-N,N-dimethyl-13-phenyl-4,6,15-trioxatetracyclo[7.6.0.0^{3,7}.0^{10,14}]pentadeca-1,3(7),8-triene-12-carboxamide

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)[C@@]12OC3=CC4=C(OCO4)C(OC)=C3[C@]1(O)[C@H](O)[C@@H]([C@H]2C1=CC=CC=C1)C(=O)N(C)C

InChI Identifier

InChI=1S/C29H29NO8/c1-30(2)27(32)21-22(16-8-6-5-7-9-16)29(17-10-12-18(34-3)13-11-17)28(33,26(21)31)23-19(38-29)14-20-24(25(23)35-4)37-15-36-20/h5-14,21-22,26,31,33H,15H2,1-4H3/t21-,22-,26-,28+,29+/m1/s1

InChI Key

VBEWJSMISIWDQM-NPWWZGLVSA-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
Aglaia edulis	Plant	KNApSAcK
Aglaia elaeagnoidea	LOTUS Database	35616633
Aglaia oligophylla	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavaglines. These are heterocyclic compounds with a structure characterized by a cyclopenta[b]benzofuran skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Flavaglines

Direct Parent

Flavaglines

Alternative Parents

Substituents

Flavagline skeleton
Stilbene
Benzodioxole
Coumaran
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tertiary carboxylic acid amide
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
1,2-diol
Carboxamide group
Oxacycle
Acetal
Ether
Carboxylic acid derivative
Organic oxide
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen 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	3.07	ALOGPS
logP	2.17	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	11.58	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	106.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.57 m³·mol⁻¹	ChemAxon
Polarizability	54.01 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00041328

Chemspider ID

23339096

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15450360

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Aglaroxin A (NP0077873)

MOL for NP0077873 ((-)-Aglaroxin A)

3D MOL for NP0077873 ((-)-Aglaroxin A)

3D SDF for NP0077873 ((-)-Aglaroxin A)

3D-SDF for NP0077873 ((-)-Aglaroxin A)

PDB for NP0077873 ((-)-Aglaroxin A)

3D PDB for NP0077873 ((-)-Aglaroxin A)

SMILES for NP0077873 ((-)-Aglaroxin A)

INCHI for NP0077873 ((-)-Aglaroxin A)

Structure for NP0077873 ((-)-Aglaroxin A)

3D Structure for NP0077873 ((-)-Aglaroxin A)