NP-MRD: Showing NP-Card for Hebevinoside XIII (NP0048019)

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Record Information

Version

2.0

Created at

2022-03-17 20:49:45 UTC

Updated at

2022-03-17 20:49:45 UTC

NP-MRD ID

NP0048019

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hebevinoside XIII

Description

Hebevinoside XIII belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. Hebevinoside XIII is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, hebevinoside XIII has been detected, but not quantified in, mushrooms. Hebevinoside XIII is found in Hebeloma vinosophyllum and Hebeloma vinosphyllum. This could make hebevinoside XIII a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307572D          

 65 70  0  0  0  0            999 V2000
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   -2.4856    5.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6631   -2.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4729    4.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061307572D          

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M  END
> <DATABASE_ID>
NP0048019

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)C)C1C(CC2(C)C3C(O)C=C4C(CCC(OC5OCC(OC(C)=O)C(OC(C)=O)C5O)C4(C)C)C3(C)CCC12C)OC1OC(COC(C)=O)C(OC(C)=O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C49H76O16/c1-24(2)14-13-15-25(3)37-33(63-45-39(56)38(55)41(61-28(6)52)35(64-45)22-58-26(4)50)21-49(12)43-32(54)20-31-30(47(43,10)18-19-48(37,49)11)16-17-36(46(31,8)9)65-44-40(57)42(62-29(7)53)34(23-59-44)60-27(5)51/h14,20,25,30,32-45,54-57H,13,15-19,21-23H2,1-12H3

> <INCHI_KEY>
UXLRAUFZYMHXTO-UHFFFAOYSA-N

> <FORMULA>
C49H76O16

> <MOLECULAR_WEIGHT>
921.1181

> <EXACT_MASS>
920.513336384

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
100.61844734824535

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[3-(acetyloxy)-6-[(5-{[4,5-bis(acetyloxy)-3-hydroxyoxan-2-yl]oxy}-9-hydroxy-1,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl)oxy]-4,5-dihydroxyoxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
4.64

> <JCHEM_LOGP>
4.141873503666666

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.59546847863032

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.003072655478348

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6143418128491894

> <JCHEM_POLAR_SURFACE_AREA>
223.0399999999999

> <JCHEM_REFRACTIVITY>
233.31240000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3-(acetyloxy)-6-[(5-{[4,5-bis(acetyloxy)-3-hydroxyoxan-2-yl]oxy}-9-hydroxy-1,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl)oxy]-4,5-dihydroxyoxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.534  12.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.640  10.840   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.302   8.829   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.238  -4.857   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.903  -0.277   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.014  -3.919   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.889   2.078   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.263   2.259   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.125   2.931   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.230   6.872   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.534   7.623   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.098   3.294   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.749   8.408   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.169   9.835   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.804   7.192   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.746   6.601   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.262   6.330   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.714   7.143   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.199   7.414   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.284   2.798   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.513   3.843   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.603  -0.833   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.355   0.537   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.114  11.050   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.279   7.403   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.509  -3.342   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.910  -1.454   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.742  -2.403   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.373   2.349   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.754   5.424   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.277   3.975   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.768   3.069   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.239   4.708   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.871   0.265   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.575   0.160   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.786   4.882   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.667   6.187   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -3.200   0.629   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.929   2.145   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      13.341   2.891   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.023  -0.363   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.864   1.443   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.245   4.518   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      11.825   3.162   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -1.481   2.669   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       8.793   3.704   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.238   5.695   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       2.206   6.237   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       2.729   4.789   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       2.957  -2.818   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      15.434  -2.902   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -4.920  -1.410   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      15.849   3.798   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       3.776   1.892   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      -4.649   0.106   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      -4.107   3.138   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      14.333   4.069   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       0.332  -2.349   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      10.832   1.985   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      13.394  -1.183   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      -2.294  -1.879   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      15.380   1.172   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      -1.210   4.185   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      -0.304   1.676   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      11.302   4.611   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2   24                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7   29                                                            
CONECT    8   46                                                            
CONECT    9   46                                                            
CONECT   10   47                                                            
CONECT   11   48                                                            
CONECT   12   49                                                            
CONECT   13   14   15                                                       
CONECT   14   13   24                                                       
CONECT   15   13   25                                                       
CONECT   16   17   30                                                       
CONECT   17   16   36                                                       
CONECT   18   19   47                                                       
CONECT   19   18   48                                                       
CONECT   20   31   32                                                       
CONECT   21   33   49                                                       
CONECT   22   35   58                                                       
CONECT   23   34   59                                                       
CONECT   24    1    2   14                                                  
CONECT   25    3   15   37                                                  
CONECT   26    4   50   58                                                  
CONECT   27    5   51   60                                                  
CONECT   28    6   52   61                                                  
CONECT   29    7   53   62                                                  
CONECT   30   16   31   47                                                  
CONECT   31   20   30   46                                                  
CONECT   32   20   43   54                                                  
CONECT   33   21   37   63                                                  
CONECT   34   23   42   60                                                  
CONECT   35   22   41   64                                                  
CONECT   36   17   46   65                                                  
CONECT   37   25   33   48                                                  
CONECT   38   39   41   55                                                  
CONECT   39   38   45   56                                                  
CONECT   40   42   44   57                                                  
CONECT   41   35   38   61                                                  
CONECT   42   34   40   62                                                  
CONECT   43   32   47   49                                                  
CONECT   44   40   59   65                                                  
CONECT   45   39   63   64                                                  
CONECT   46    8    9   31   36                                             
CONECT   47   10   18   30   43                                             
CONECT   48   11   19   37   49                                             
CONECT   49   12   21   43   48                                             
CONECT   50   26                                                            
CONECT   51   27                                                            
CONECT   52   28                                                            
CONECT   53   29                                                            
CONECT   54   32                                                            
CONECT   55   38                                                            
CONECT   56   39                                                            
CONECT   57   40                                                            
CONECT   58   22   26                                                       
CONECT   59   23   44                                                       
CONECT   60   27   34                                                       
CONECT   61   28   41                                                       
CONECT   62   29   42                                                       
CONECT   63   33   45                                                       
CONECT   64   35   45                                                       
CONECT   65   36   44                                                       
MASTER        0    0    0    0    0    0    0    0   65    0  140    0
END

View in JSmol

Synonyms

Value	Source
[3-(Acetyloxy)-6-[(5-{[4,5-bis(acetyloxy)-3-hydroxyoxan-2-yl]oxy}-9-hydroxy-1,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl)oxy]-4,5-dihydroxyoxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₄₉H₇₆O₁₆

Average Mass

921.1181 Da

Monoisotopic Mass

920.51334 Da

IUPAC Name

[3-(acetyloxy)-6-[(5-{[4,5-bis(acetyloxy)-3-hydroxyoxan-2-yl]oxy}-9-hydroxy-1,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl)oxy]-4,5-dihydroxyoxan-2-yl]methyl acetate

Traditional Name

CAS Registry Number

138995-52-5

SMILES

CC(CCC=C(C)C)C1C(CC2(C)C3C(O)C=C4C(CCC(OC5OCC(OC(C)=O)C(OC(C)=O)C5O)C4(C)C)C3(C)CCC12C)OC1OC(COC(C)=O)C(OC(C)=O)C(O)C1O

InChI Identifier

InChI=1S/C49H76O16/c1-24(2)14-13-15-25(3)37-33(63-45-39(56)38(55)41(61-28(6)52)35(64-45)22-58-26(4)50)21-49(12)43-32(54)20-31-30(47(43,10)18-19-48(37,49)11)16-17-36(46(31,8)9)65-44-40(57)42(62-29(7)53)34(23-59-44)60-27(5)51/h14,20,25,30,32-45,54-57H,13,15-19,21-23H2,1-12H3

InChI Key

UXLRAUFZYMHXTO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Hebeloma vinosophyllum	LOTUS Database	35616633
Hebeloma vinosphyllum	Fungi	KNApSAcK
Pleurotus ostreatus	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 cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

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	4.64	ALOGPS
logP	4.14	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	12	ChemAxon
pKa (Strongest Basic)	-0.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	223.04 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	233.31 m³·mol⁻¹	ChemAxon
Polarizability	100.62 Å³	ChemAxon
Number of Rings	6	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

HMDB0034603

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013119

KNApSAcK ID

C00023927

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751589

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Hebevinoside XIII (NP0048019)

MOL for NP0048019 (Hebevinoside XIII)

3D MOL for NP0048019 (Hebevinoside XIII)

3D SDF for NP0048019 (Hebevinoside XIII)

3D-SDF for NP0048019 (Hebevinoside XIII)

PDB for NP0048019 (Hebevinoside XIII)

3D PDB for NP0048019 (Hebevinoside XIII)

SMILES for NP0048019 (Hebevinoside XIII)

INCHI for NP0048019 (Hebevinoside XIII)

Structure for NP0048019 (Hebevinoside XIII)

3D Structure for NP0048019 (Hebevinoside XIII)