NP-MRD: Showing NP-Card for Mahmoodin (NP0084189)

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Record Information

Version

2.0

Created at

2022-04-29 04:59:42 UTC

Updated at

2022-04-29 04:59:42 UTC

NP-MRD ID

NP0084189

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mahmoodin

Description

Mahmoodin belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Mahmoodin is found in Azadirachta indica . Mahmoodin was first documented in 2013 (PMID: 24075352). Based on a literature review very few articles have been published on Mahmoodin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206592D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292206592D          

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    1.8355   -2.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2931   -3.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167   -4.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5209   -4.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732   -1.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 34  1  6  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 34 38  1  0  0  0  0
 29 39  1  0  0  0  0
  2 39  1  0  0  0  0
 18 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084189

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC[C@]3(C)C(=CC(=O)O[C@@]3(OCCO)C3=COC=C3)[C@]1(C)[C@@H](C[C@@]1([H])C(C)(C)C(=O)C=C[C@]21C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O8/c1-18(32)37-24-15-21-26(2,3)23(33)8-10-27(21,4)20-7-11-28(5)22(29(20,24)6)16-25(34)38-30(28,36-14-12-31)19-9-13-35-17-19/h8-10,13,16-17,20-21,24,31H,7,11-12,14-15H2,1-6H3/t20-,21+,24-,27-,28-,29-,30+/m1/s1

> <INCHI_KEY>
HGUQPCAWIZIAKO-GALXXUDFSA-N

> <FORMULA>
C30H38O8

> <MOLECULAR_WEIGHT>
526.626

> <EXACT_MASS>
526.256668184

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.62047898381695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,6R,7R,10R,11R,16R,18R)-6-(furan-3-yl)-6-(2-hydroxyethoxy)-1,7,11,15,15-pentamethyl-4,14-dioxo-5-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-2,12-dien-18-yl acetate

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
4.651763494666666

> <ALOGPS_LOGS>
-4.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.114079557047013

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7489016017476366

> <JCHEM_POLAR_SURFACE_AREA>
112.27000000000001

> <JCHEM_REFRACTIVITY>
139.28229999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6R,7R,10R,11R,16R,18R)-6-(furan-3-yl)-6-(2-hydroxyethoxy)-1,7,11,15,15-pentamethyl-4,14-dioxo-5-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-2,12-dien-18-yl acetate

> <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  O   UNK     0       4.652  -1.522   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.660  -2.686   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.685  -2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.189  -0.649   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.693   0.807   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.685   1.971   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.205   1.098   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      13.726  -3.850   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.551  -1.604   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.680  -0.956   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.709  -5.596   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       9.189  -4.723   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0      10.197  -5.887   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.685  -6.178   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.172  -6.469   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.714  -6.744   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.742  -7.939   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.291  -9.378   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.320 -10.573   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.843  -6.096   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.426  -5.492   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.414  -6.652   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.205  -7.973   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.706  -7.630   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       5.156  -4.141   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      16.750  -3.268   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6    7   23                                             
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14   15   21                                             
CONECT   14   13                                                            
CONECT   15   13   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19   40                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   13   22   23                                             
CONECT   22   21                                                            
CONECT   23   21    5   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    4   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30   34   39                                             
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   29   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   34                                                       
CONECT   39   29    2                                                       
CONECT   40   18                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
17-Glycolyldeoxygedunin	MeSH

Chemical Formula

C₃₀H₃₈O₈

Average Mass

526.6260 Da

Monoisotopic Mass

526.25667 Da

IUPAC Name

(1R,6R,7R,10R,11R,16R,18R)-6-(furan-3-yl)-6-(2-hydroxyethoxy)-1,7,11,15,15-pentamethyl-4,14-dioxo-5-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-2,12-dien-18-yl acetate

Traditional Name

(1R,6R,7R,10R,11R,16R,18R)-6-(furan-3-yl)-6-(2-hydroxyethoxy)-1,7,11,15,15-pentamethyl-4,14-dioxo-5-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-2,12-dien-18-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@]12CC[C@]3(C)C(=CC(=O)O[C@@]3(OCCO)C3=COC=C3)[C@]1(C)[C@@H](C[C@@]1([H])C(C)(C)C(=O)C=C[C@]21C)OC(C)=O

InChI Identifier

InChI=1S/C30H38O8/c1-18(32)37-24-15-21-26(2,3)23(33)8-10-27(21,4)20-7-11-28(5)22(29(20,24)6)16-25(34)38-30(28,36-14-12-31)19-9-13-35-17-19/h8-10,13,16-17,20-21,24,31H,7,11-12,14-15H2,1-6H3/t20-,21+,24-,27-,28-,29-,30+/m1/s1

InChI Key

HGUQPCAWIZIAKO-GALXXUDFSA-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
Azadirachta indica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five 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

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Ketal
Cyclohexenone
Dihydropyranone
Dicarboxylic acid or derivatives
Pyran
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Cyclic ketone
Ketone
Lactone
Acetal
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Primary 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
logP	4.27	ALOGPS
logP	4.65	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	15.11	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	112.27 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.28 m³·mol⁻¹	ChemAxon
Polarizability	55.62 Å³	ChemAxon
Number of Rings	5	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

C00053452

Chemspider ID

112458

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

126566

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Koriem KM: Review on pharmacological and toxicologyical effects of oleum azadirachti oil. Asian Pac J Trop Biomed. 2013 Oct;3(10):834-40. doi: 10.1016/S2221-1691(13)60165-3. Epub 2013 Sep 4. [PubMed:24075352 ]

Showing NP-Card for Mahmoodin (NP0084189)

MOL for NP0084189 (Mahmoodin)

3D MOL for NP0084189 (Mahmoodin)

3D SDF for NP0084189 (Mahmoodin)

3D-SDF for NP0084189 (Mahmoodin)

PDB for NP0084189 (Mahmoodin)

3D PDB for NP0084189 (Mahmoodin)

SMILES for NP0084189 (Mahmoodin)

INCHI for NP0084189 (Mahmoodin)

Structure for NP0084189 (Mahmoodin)

3D Structure for NP0084189 (Mahmoodin)