NP-MRD: Showing NP-Card for (+)-Azedararide (NP0077531)

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Record Information

Version

2.0

Created at

2022-04-28 22:40:05 UTC

Updated at

2022-04-28 22:40:05 UTC

NP-MRD ID

NP0077531

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Azedararide

Description

Azedaralide belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. (+)-Azedararide is found in Melia azedarach . (+)-Azedararide was first documented in 2011 (PMID: 21258734). Based on a literature review very few articles have been published on Azedaralide (PMID: 22994389).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    0.4944   -1.1022    1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1848   -0.1468   -0.0017 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1669   -0.9926   -1.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8803   -2.0871   -1.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2148   -1.5679   -0.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3677   -0.4339   -0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7757    0.0440   -0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9623    1.2677   -0.6223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2249    0.3346    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4647    1.4511    0.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3723    2.2705    1.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6408    3.3437    1.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9079    1.8199    1.1110 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524    0.9622   -0.0374 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5728    0.6790    0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126   -0.4703   -0.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6612   -0.1093    0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6980    1.1873    0.1710 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218    1.7053    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1857   -0.5888    1.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4371   -1.3147    1.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9317   -2.0316    0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1047   -1.4920   -1.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1037   -0.3340   -2.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8649   -2.5991   -2.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5376   -2.7812   -0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0754   -2.1327   -1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0109    0.0546    1.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4977   -0.6594   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6813    1.7823   -0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159    1.7889    1.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9076    1.6499   -0.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0041   -1.4781   -0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4945   -0.7826    0.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3271    2.7633    0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 19  2  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
  9  2  1  0
 16 15  1  0
 14  2  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
 10 31  1  0
 14 32  1  6
 19 35  1  0
 17 34  1  0
 16 33  1  0
M  END


  Mrv1652304292200402D          

 19 21  0  0  1  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5253   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -3.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 10 12  1  1  0  0  0
  9 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 13 17  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077531

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CCC=C(CO)C1=CC(=O)O[C@H]2C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-15-5-2-3-10(8-16)12(15)7-13(17)19-14(15)11-4-6-18-9-11/h3-4,6-7,9,14,16H,2,5,8H2,1H3/t14-,15+/m0/s1

> <INCHI_KEY>
OVWYWAKWCKVABI-LSDHHAIUSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.289

> <EXACT_MASS>
260.104858995

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.840184162795865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8aR)-1-(furan-3-yl)-5-(hydroxymethyl)-8a-methyl-3,7,8,8a-tetrahydro-1H-isochromen-3-one

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
1.7621773349999998

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.12515649053742

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8296129627296582

> <JCHEM_POLAR_SURFACE_AREA>
59.67

> <JCHEM_REFRACTIVITY>
70.5234

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8aR)-1-(furan-3-yl)-5-(hydroxymethyl)-8a-methyl-7,8-dihydro-1H-isochromen-3-one

> <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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.581  -5.525   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.105  -6.990   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.565  -6.990   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.089  -5.525   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9    4   11   12                                             
CONECT   11   10    1                                                       
CONECT   12   10                                                            
CONECT   13    9   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
CONECT   18    3   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₄

Average Mass

260.2890 Da

Monoisotopic Mass

260.10486 Da

IUPAC Name

(1R,8aR)-1-(furan-3-yl)-5-(hydroxymethyl)-8a-methyl-3,7,8,8a-tetrahydro-1H-isochromen-3-one

Traditional Name

(1R,8aR)-1-(furan-3-yl)-5-(hydroxymethyl)-8a-methyl-7,8-dihydro-1H-isochromen-3-one

CAS Registry Number

Not Available

SMILES

C[C@@]12CCC=C(CO)C1=CC(=O)O[C@H]2C1=COC=C1

InChI Identifier

InChI=1S/C15H16O4/c1-15-5-2-3-10(8-16)12(15)7-13(17)19-14(15)11-4-6-18-9-11/h3-4,6-7,9,14,16H,2,5,8H2,1H3/t14-,15+/m0/s1

InChI Key

OVWYWAKWCKVABI-LSDHHAIUSA-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
Melia azedarach	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Primary 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	2.45	ALOGPS
logP	1.76	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	17.13	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.52 m³·mol⁻¹	ChemAxon
Polarizability	26.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

Chemspider ID

8858104

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10682758

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Faber JM, Eger WA, Williams CM: Enantioselective total synthesis of the mexicanolides: khayasin, proceranolide, and mexicanolide. J Org Chem. 2012 Oct 19;77(20):8913-21. doi: 10.1021/jo301182f. Epub 2012 Sep 20. [PubMed:22994389 ]
Faber JM, Williams CM: A concise total synthesis of (+/-)-cipadonoid B from synthetic azedaralide. Chem Commun (Camb). 2011 Feb 28;47(8):2258-60. doi: 10.1039/c0cc04698a. Epub 2011 Jan 24. [PubMed:21258734 ]

Showing NP-Card for (+)-Azedararide (NP0077531)

MOL for NP0077531 ((+)-Azedararide)

3D MOL for NP0077531 ((+)-Azedararide)

3D SDF for NP0077531 ((+)-Azedararide)

3D-SDF for NP0077531 ((+)-Azedararide)

PDB for NP0077531 ((+)-Azedararide)

3D PDB for NP0077531 ((+)-Azedararide)

SMILES for NP0077531 ((+)-Azedararide)

INCHI for NP0077531 ((+)-Azedararide)

Structure for NP0077531 ((+)-Azedararide)

3D Structure for NP0077531 ((+)-Azedararide)