NP-MRD: Showing NP-Card for Alliofuroside A (NP0049775)

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Record Information

Version

2.0

Created at

2022-03-17 21:17:56 UTC

Updated at

2022-03-17 21:17:56 UTC

NP-MRD ID

NP0049775

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Alliofuroside A

Description

Alliofuroside A belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. Alliofuroside A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, alliofuroside a is found, on average, in the highest concentration in garden onions. Alliofuroside a has also been detected, but not quantified in, onion-family vegetables. This could make alliofuroside a a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241211552D          

 62 69  0  0  0  0            999 V2000
   -4.2278   -1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2278   -2.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116   -1.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116   -2.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9439   -2.8879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986   -2.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986   -1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0858   -2.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7986   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3729   -1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0858   -0.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  2  5  1  0  0  0  0
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  3 11  1  0  0  0  0
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  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
  9 15  1  0  0  0  0
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 12 13  1  0  0  0  0
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 15 18  1  0  0  0  0
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 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 19 21  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 23 24  1  0  0  0  0
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 57 60  1  0  0  0  0
 59 61  1  0  0  0  0
M  END


  Mrv0541 02241211552D          

 62 69  0  0  0  0            999 V2000
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   -4.2278   -2.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116   -1.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7986   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0049775

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC1(O)OC2CC3C4CC=C5CC(O)CC(OC6OCC(O)C(O)C6OC6OC(C)C(O)C(O)C6O)C5(C)C4CCC3(C)C2C1C)COC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C44H72O18/c1-18(16-56-39-36(53)35(52)33(50)28(15-45)59-39)8-11-44(55)19(2)30-27(62-44)14-25-23-7-6-21-12-22(46)13-29(43(21,5)24(23)9-10-42(25,30)4)60-41-38(32(49)26(47)17-57-41)61-40-37(54)34(51)31(48)20(3)58-40/h6,18-20,22-41,45-55H,7-17H2,1-5H3

> <INCHI_KEY>
HWYCRLFVQVFKPD-UHFFFAOYSA-N

> <FORMULA>
C44H72O18

> <MOLECULAR_WEIGHT>
889.0317

> <EXACT_MASS>
888.4718655

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
94.07644567421751

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2-{[6,16-dihydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-14-yl]oxy}-4,5-dihydroxyoxan-3-yl)oxy]-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.35

> <JCHEM_LOGP>
-1.1732652196666662

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.050769612662267

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.560616695199117

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121826294395296

> <JCHEM_POLAR_SURFACE_AREA>
287.14

> <JCHEM_REFRACTIVITY>
214.98160000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2-{[6,16-dihydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-14-yl]oxy}-4,5-dihydroxyoxan-3-yl)oxy]-6-methyloxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
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HETATM    2  C   UNK     0      -7.892  -4.621   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.555  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.555  -5.391   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -9.229  -5.391   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.224  -4.621   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.224  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.893  -5.391   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.893  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.224  -1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.555  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.563  -4.621   0.000  0.00  0.00           C+0
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HETATM   14  C   UNK     0      -1.232  -2.310   0.000  0.00  0.00           C+0
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HETATM   16  C   UNK     0      -1.232  -0.776   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.222  -2.785   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.563  -0.018   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.222  -0.314   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.232   0.764   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.109  -1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.551  -1.078   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.109   0.899   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.551   0.431   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.887   1.201   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.551   1.971   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.218   0.431   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.555   1.201   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.892   0.431   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.555   2.741   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.229   1.201   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.566   0.431   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.555   0.770   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.584  -1.109   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.927   1.177   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.927  -1.867   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.246  -1.109   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.933  -3.413   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.246   0.431   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      14.576  -1.879   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      14.576   1.208   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      11.933   2.717   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      10.597  -4.189   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -5.224   1.546   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -7.892   1.546   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -5.224   3.093   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -6.555   3.851   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -7.892   3.093   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -6.555   5.391   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -9.223   3.869   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -9.229   0.776   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0     -10.566   0.006   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -11.927   0.739   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0     -10.566  -1.540   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0     -13.246   0.006   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0     -11.933   2.286   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0     -13.246  -1.540   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0     -14.570   0.788   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0     -11.927  -2.286   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0     -14.576  -2.317   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0     -11.933  -3.826   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       0.634   2.366   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5                                                  
CONECT    3    1    7   11                                                  
CONECT    4    2    6                                                       
CONECT    5    2                                                            
CONECT    6    4    7    8                                                  
CONECT    7    3    6    9   10                                             
CONECT    8    6   12                                                       
CONECT    9    7   13   15                                                  
CONECT   10    7                                                            
CONECT   11    3   33                                                       
CONECT   12    8   13                                                       
CONECT   13    9   12   14                                                  
CONECT   14   13   16   17                                                  
CONECT   15    9   18                                                       
CONECT   16   14   18   19   20                                             
CONECT   17   14   21                                                       
CONECT   18   15   16                                                       
CONECT   19   16   21   23                                                  
CONECT   20   16                                                            
CONECT   21   17   19   22                                                  
CONECT   22   21   24                                                       
CONECT   23   19   24   62                                                  
CONECT   24   22   23   25   26                                             
CONECT   25   24   27                                                       
CONECT   26   24                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28   31                                                       
CONECT   30   28                                                            
CONECT   31   29   32                                                       
CONECT   32   31   34   35                                                  
CONECT   33   11   44   45                                                  
CONECT   34   32   36                                                       
CONECT   35   32   39   42                                                  
CONECT   36   34   37   38                                                  
CONECT   37   36   39   40                                                  
CONECT   38   36   43                                                       
CONECT   39   35   37   41                                                  
CONECT   40   37                                                            
CONECT   41   39                                                            
CONECT   42   35                                                            
CONECT   43   38                                                            
CONECT   44   33   46                                                       
CONECT   45   33   48   51                                                  
CONECT   46   44   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   45   47   50                                                  
CONECT   49   47                                                            
CONECT   50   48                                                            
CONECT   51   45   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52   55   56                                                  
CONECT   54   52   59                                                       
CONECT   55   53   57   58                                                  
CONECT   56   53                                                            
CONECT   57   55   59   60                                                  
CONECT   58   55                                                            
CONECT   59   54   57   61                                                  
CONECT   60   57                                                            
CONECT   61   59                                                            
CONECT   62   23                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  138    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₄H₇₂O₁₈

Average Mass

889.0317 Da

Monoisotopic Mass

888.47187 Da

IUPAC Name

2-[(2-{[6,16-dihydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-14-yl]oxy}-4,5-dihydroxyoxan-3-yl)oxy]-6-methyloxane-3,4,5-triol

Traditional Name

CAS Registry Number

105798-62-7

SMILES

CC(CCC1(O)OC2CC3C4CC=C5CC(O)CC(OC6OCC(O)C(O)C6OC6OC(C)C(O)C(O)C6O)C5(C)C4CCC3(C)C2C1C)COC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C44H72O18/c1-18(16-56-39-36(53)35(52)33(50)28(15-45)59-39)8-11-44(55)19(2)30-27(62-44)14-25-23-7-6-21-12-22(46)13-29(43(21,5)24(23)9-10-42(25,30)4)60-41-38(32(49)26(47)17-57-41)61-40-37(54)34(51)31(48)20(3)58-40/h6,18-20,22-41,45-55H,7-17H2,1-5H3

InChI Key

HWYCRLFVQVFKPD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Allium cepa	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium fistulosum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal saponins

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic 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	-0.35	ALOGPS
logP	-1.2	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.56	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	287.14 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	214.98 m³·mol⁻¹	ChemAxon
Polarizability	94.08 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0041051

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020924

KNApSAcK ID

Not Available

Chemspider ID

4159815

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4979367

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Alliofuroside A (NP0049775)

MOL for NP0049775 (Alliofuroside A)

3D MOL for NP0049775 (Alliofuroside A)

3D SDF for NP0049775 (Alliofuroside A)

3D-SDF for NP0049775 (Alliofuroside A)

PDB for NP0049775 (Alliofuroside A)

3D PDB for NP0049775 (Alliofuroside A)

SMILES for NP0049775 (Alliofuroside A)

INCHI for NP0049775 (Alliofuroside A)

Structure for NP0049775 (Alliofuroside A)

3D Structure for NP0049775 (Alliofuroside A)