NP-MRD: Showing NP-Card for methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate (NP0252293)

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Record Information

Version

2.0

Created at

2022-09-07 15:45:23 UTC

Updated at

2022-09-07 15:45:23 UTC

NP-MRD ID

NP0252293

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate

Description

CHEMBL1774411 belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate is found in Azadirachta indica. Based on a literature review very few articles have been published on CHEMBL1774411.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217452D          

 35 39  0  0  1  0            999 V2000
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    3.1610   -1.4239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072217452D          

 35 39  0  0  1  0            999 V2000
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 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 23 33  1  0  0  0  0
 33 34  1  0  0  0  0
 21 34  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0252293

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1[C@@]2(C)[C@H](O[C@@H]3C[C@H](C(C)=C23)C2=COC=C2)[C@H](OC(C)=O)[C@H]2[C@](C)(O)C=CC(=O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O8/c1-13-16(15-8-10-33-12-15)11-17-19(13)27(5)22(24(30)32-6)26(4)18(29)7-9-25(3,31)21(26)20(23(27)35-17)34-14(2)28/h7-10,12,16-17,20-23,31H,11H2,1-6H3/t16-,17-,20-,21+,22-,23-,25-,26+,27+/m1/s1

> <INCHI_KEY>
WMLLQNMCBDBSNU-YWHYXYIKSA-N

> <FORMULA>
C27H32O8

> <MOLECULAR_WEIGHT>
484.545

> <EXACT_MASS>
484.20971799

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.87367758032722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,2R,3S,4R,8S,9S,10R,13R,15R)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0^{3,8}.0^{11,15}]hexadeca-5,11-diene-9-carboxylate

> <JCHEM_LOGP>
2.0445825123333323

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.246978951127033

> <JCHEM_PKA_STRONGEST_BASIC>
-2.859216674000095

> <JCHEM_POLAR_SURFACE_AREA>
112.27000000000001

> <JCHEM_REFRACTIVITY>
125.24749999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2R,3S,4R,8S,9S,10R,13R,15R)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0^{3,8}.0^{11,15}]hexadeca-5,11-diene-9-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       5.622  -1.143   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.900  -2.658   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.351  -3.174   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.524  -2.176   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.630  -4.689   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.081  -5.205   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.802  -3.690   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.253  -4.206   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.975  -2.692   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.704  -4.722   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.983  -6.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.810  -7.235   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.997  -8.217   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.050  -8.575   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.359  -6.719   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.187  -7.718   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.465  -9.232   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.916  -9.749   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.089  -8.750   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.195 -11.263   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.736  -7.202   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.382  -7.935   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.266  -6.873   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.739  -6.670   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.461  -5.155   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.072  -4.490   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.283  -5.223   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.398  -4.162   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.733  -2.772   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.793  -2.976   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.815  -4.422   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.019  -2.896   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.931  -5.484   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.457  -5.687   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.022  -4.210   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   34                                                  
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12    6   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22   34                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   33                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   26                                                       
CONECT   31   25   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   23   34                                                  
CONECT   34   33   21    5   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₈

Average Mass

484.5450 Da

Monoisotopic Mass

484.20972 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H]1[C@@]2(C)[C@H](O[C@@H]3C[C@H](C(C)=C23)C2=COC=C2)[C@H](OC(C)=O)[C@H]2[C@](C)(O)C=CC(=O)[C@]12C

InChI Identifier

InChI=1S/C27H32O8/c1-13-16(15-8-10-33-12-15)11-17-19(13)27(5)22(24(30)32-6)26(4)18(29)7-9-25(3,31)21(26)20(23(27)35-17)34-14(2)28/h7-10,12,16-17,20-23,31H,11H2,1-6H3/t16-,17-,20-,21+,22-,23-,25-,26+,27+/m1/s1

InChI Key

WMLLQNMCBDBSNU-YWHYXYIKSA-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
Azadirachta indica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Cyclohexenone
Dicarboxylic acid or derivatives
Furan
Heteroaromatic compound
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
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

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

26346476

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54585273

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate (NP0252293)

MOL for NP0252293 (methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate)

3D MOL for NP0252293 (methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate)

3D SDF for NP0252293 (methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate)

3D-SDF for NP0252293 (methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate)

PDB for NP0252293 (methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate)

3D PDB for NP0252293 (methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate)

SMILES for NP0252293 (methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate)

INCHI for NP0252293 (methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate)

Structure for NP0252293 (methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate)

3D Structure for NP0252293 (methyl (1s,2r,3s,4r,8s,9s,10r,13r,15r)-2-(acetyloxy)-13-(furan-3-yl)-4-hydroxy-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-5,11-diene-9-carboxylate)