NP-MRD: Showing NP-Card for (+)-Aglaroxin D (NP0075074)

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Record Information

Version

2.0

Created at

2022-04-28 20:23:23 UTC

Updated at

2022-04-28 20:23:23 UTC

NP-MRD ID

NP0075074

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Aglaroxin D

Description

Aglaiastatin belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. (+)-Aglaroxin D is found in Aglaia elaeagnoidea, Aglaia gracilis and Aglaia odorata. (+)-Aglaroxin D was first documented in 2004 (PMID: 15027128). Based on a literature review a small amount of articles have been published on Aglaiastatin (PMID: 25514979) (PMID: 30718665).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222232D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282222232D          

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 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
  9 27  1  6  0  0  0
  8 28  1  6  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
  1 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075074

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)[C@@]12OC3=CC(OC)=CC(OC)=C3[C@]1(O)C1=C([C@H]2C2=CC=CC=C2)C(=O)N2CCC[C@H]2N1

> <INCHI_IDENTIFIER>
InChI=1S/C31H30N2O6/c1-36-20-13-11-19(12-14-20)31-26(18-8-5-4-6-9-18)25-28(32-24-10-7-15-33(24)29(25)34)30(31,35)27-22(38-3)16-21(37-2)17-23(27)39-31/h4-6,8-9,11-14,16-17,24,26,32,35H,7,10,15H2,1-3H3/t24-,26+,30-,31-/m0/s1

> <INCHI_KEY>
HSVMIKSELPDICN-OTEJJTPWSA-N

> <FORMULA>
C31H30N2O6

> <MOLECULAR_WEIGHT>
526.589

> <EXACT_MASS>
526.210386694

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
56.07637415224409

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,10R,11R,18S)-2-hydroxy-4,6-dimethoxy-10-(4-methoxyphenyl)-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0^{2,10}.0^{3,8}.0^{14,18}]nonadeca-1(12),3,5,7-tetraen-13-one

> <ALOGPS_LOGP>
3.51

> <JCHEM_LOGP>
2.769824561

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.721950053417128

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.708220747842107

> <JCHEM_PKA_STRONGEST_BASIC>
-0.16043837502935443

> <JCHEM_POLAR_SURFACE_AREA>
89.49000000000001

> <JCHEM_REFRACTIVITY>
144.52029999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,10R,11R,18S)-2-hydroxy-4,6-dimethoxy-10-(4-methoxyphenyl)-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0^{2,10}.0^{3,8}.0^{14,18}]nonadeca-1(12),3,5,7-tetraen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      12.063   3.269   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.954   4.337   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.474   3.911   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.103   2.417   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.212   1.348   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.692   1.774   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.538  -0.037   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.013   0.176   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.744   1.692   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.219   1.905   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.545   0.520   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.654  -0.548   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.981  -1.933   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.843  -3.209   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.170  -4.594   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.633  -4.703   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.771  -3.427   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.445  -2.042   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.009   0.411   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.336  -0.974   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       3.147   1.687   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       3.820   3.072   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       5.356   3.181   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       2.711   4.140   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.352   3.416   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.621   1.900   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.475   3.209   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.282  -1.340   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.730  -1.865   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.999  -3.382   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.820  -4.373   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.373  -3.848   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.104  -2.331   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.089  -5.889   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.537  -6.414   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.365   4.980   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.736   6.475   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      13.543   3.695   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      13.914   5.190   0.000  0.00  0.00           C+0
CONECT    1    2    6   38                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12   28                                             
CONECT    9    8    4   10   27                                             
CONECT   10    9   11   23                                                  
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   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   10                                                       
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27    9                                                            
CONECT   28    8   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   31   35                                                       
CONECT   35   34                                                            
CONECT   36    3   37                                                       
CONECT   37   36                                                            
CONECT   38    1   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₀N₂O₆

Average Mass

526.5890 Da

Monoisotopic Mass

526.21039 Da

IUPAC Name

(2S,10R,11R,18S)-2-hydroxy-4,6-dimethoxy-10-(4-methoxyphenyl)-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0^{2,10}.0^{3,8}.0^{14,18}]nonadeca-1(12),3,5,7-tetraen-13-one

Traditional Name

(2S,10R,11R,18S)-2-hydroxy-4,6-dimethoxy-10-(4-methoxyphenyl)-11-phenyl-9-oxa-14,19-diazapentacyclo[10.7.0.0^{2,10}.0^{3,8}.0^{14,18}]nonadeca-1(12),3,5,7-tetraen-13-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)[C@@]12OC3=CC(OC)=CC(OC)=C3[C@]1(O)C1=C([C@H]2C2=CC=CC=C2)C(=O)N2CCC[C@H]2N1

InChI Identifier

InChI=1S/C31H30N2O6/c1-36-20-13-11-19(12-14-20)31-26(18-8-5-4-6-9-18)25-28(32-24-10-7-15-33(24)29(25)34)30(31,35)27-22(38-3)16-21(37-2)17-23(27)39-31/h4-6,8-9,11-14,16-17,24,26,32,35H,7,10,15H2,1-3H3/t24-,26+,30-,31-/m0/s1

InChI Key

HSVMIKSELPDICN-OTEJJTPWSA-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 elaeagnoidea	LOTUS Database	35616633
Aglaia gracilis	Plant	KNApSAcK
Aglaia odorata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Coumaran
Anisole
Phenol ether
Methoxybenzene
Phenoxy compound
Alkyl aryl ether
Monocyclic benzene moiety
Hydropyrimidine
1,2,3,4-tetrahydropyrimidine
Benzenoid
Vinylogous amide
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrrolidine
Carboxamide group
Lactam
Azacycle
Ether
Enamine
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Amine
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic nitrogen 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	3.51	ALOGPS
logP	2.77	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.49 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	144.52 m³·mol⁻¹	ChemAxon
Polarizability	56.08 Å³	ChemAxon
Number of Rings	7	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

C00036692

Chemspider ID

8047223

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9871534

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stone SD, Lajkiewicz NJ, Whitesell L, Hilmy A, Porco JA Jr: Biomimetic kinetic resolution: highly enantio- and diastereoselective transfer hydrogenation of aglain ketones to access flavagline natural products. J Am Chem Soc. 2015 Jan 14;137(1):525-30. doi: 10.1021/ja511728b. Epub 2014 Dec 29. [PubMed:25514979 ]
Itoua Maiga R, Cencic R, Chu J, Waller DD, Brown LE, Devine WG, Zhang W, Sebag M, Porco JA Jr, Pelletier J: Oxo-aglaiastatin-Mediated Inhibition of Translation Initiation. Sci Rep. 2019 Feb 4;9(1):1265. doi: 10.1038/s41598-018-37666-5. [PubMed:30718665 ]
Hausott B, Greger H, Marian B: Flavaglines: a group of efficient growth inhibitors block cell cycle progression and induce apoptosis in colorectal cancer cells. Int J Cancer. 2004 May 10;109(6):933-40. doi: 10.1002/ijc.20033. [PubMed:15027128 ]

Showing NP-Card for (+)-Aglaroxin D (NP0075074)

MOL for NP0075074 ((+)-Aglaroxin D)

3D MOL for NP0075074 ((+)-Aglaroxin D)

3D SDF for NP0075074 ((+)-Aglaroxin D)

3D-SDF for NP0075074 ((+)-Aglaroxin D)

PDB for NP0075074 ((+)-Aglaroxin D)

3D PDB for NP0075074 ((+)-Aglaroxin D)

SMILES for NP0075074 ((+)-Aglaroxin D)

INCHI for NP0075074 ((+)-Aglaroxin D)

Structure for NP0075074 ((+)-Aglaroxin D)

3D Structure for NP0075074 ((+)-Aglaroxin D)