NP-MRD: Showing NP-Card for Hebevinoside XIV (NP0048020)

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Record Information

Version

2.0

Created at

2022-03-17 20:49:46 UTC

Updated at

2022-03-17 20:49:46 UTC

NP-MRD ID

NP0048020

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hebevinoside XIV

Description

Hebevinoside XIV 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 XIV is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, hebevinoside XIV has been detected, but not quantified in, mushrooms. Hebevinoside XIV is found in Hebeloma vinosophyllum and Hebeloma vinosphyllum. This could make hebevinoside XIV a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307572D          

 62 67  0  0  0  0            999 V2000
   -1.3574    6.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    8.5195   -0.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5832    1.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4264    1.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4239    1.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8218    4.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6596    1.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729    4.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1620    5.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9665    3.8530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1498    3.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9620    3.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 13 12  1  0  0  0  0
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 16 15  1  0  0  0  0
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 62 42  1  0  0  0  0
M  END


  Mrv0541 05061307572D          

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    5.4239    1.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377    3.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8218    4.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0048020

> <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(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C47H74O15/c1-23(2)13-12-14-24(3)35-31(60-43-38(54)37(53)36(52)32(61-43)21-56-25(4)48)20-47(11)41-30(51)19-29-28(45(41,9)17-18-46(35,47)10)15-16-34(44(29,7)8)62-42-39(55)40(59-27(6)50)33(22-57-42)58-26(5)49/h13,19,24,28,30-43,51-55H,12,14-18,20-22H2,1-11H3

> <INCHI_KEY>
HZVGDAABVDIGIT-UHFFFAOYSA-N

> <FORMULA>
C47H74O15

> <MOLECULAR_WEIGHT>
879.0815

> <EXACT_MASS>
878.502771698

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
96.22637535666746

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{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]-3,4,5-trihydroxyoxan-2-yl}methyl acetate

> <ALOGPS_LOGP>
4.17

> <JCHEM_LOGP>
3.700748093333332

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.527273905405178

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.970236905353467

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6144140638768206

> <JCHEM_POLAR_SURFACE_AREA>
216.9699999999999

> <JCHEM_REFRACTIVITY>
224.1609

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{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]-3,4,5-trihydroxyoxan-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      17.889   2.078   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.263   2.259   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.125   2.931   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.230   6.872   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.534   7.623   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.098   3.294   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.749   8.408   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.169   9.835   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.804   7.192   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.746   6.601   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.262   6.330   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.714   7.143   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.199   7.414   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.284   2.798   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.513   3.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.603  -0.833   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.355   0.537   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.114  11.050   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.279   7.403   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.509  -3.342   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.910  -1.454   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.373   2.349   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.754   5.424   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.277   3.975   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.768   3.069   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.239   4.708   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.575   0.160   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.871   0.265   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.786   4.882   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.667   6.187   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.023  -0.363   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.200   0.629   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.929   2.145   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.341   2.891   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      13.864   1.443   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.245   4.518   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      11.825   3.162   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -1.481   2.669   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.793   3.704   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       5.238   5.695   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       2.206   6.237   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.729   4.789   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       2.957  -2.818   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      15.434  -2.902   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      15.849   3.798   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       3.776   1.892   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -2.294  -1.879   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -4.649   0.106   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      -4.107   3.138   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      14.333   4.069   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       0.332  -2.349   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      10.832   1.985   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      13.394  -1.183   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      15.380   1.172   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      -1.210   4.185   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      -0.304   1.676   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      11.302   4.611   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5   26                                                            
CONECT    6   27                                                            
CONECT    7   44                                                            
CONECT    8   44                                                            
CONECT    9   45                                                            
CONECT   10   46                                                            
CONECT   11   47                                                            
CONECT   12   13   14                                                       
CONECT   13   12   23                                                       
CONECT   14   12   24                                                       
CONECT   15   16   28                                                       
CONECT   16   15   34                                                       
CONECT   17   18   45                                                       
CONECT   18   17   46                                                       
CONECT   19   29   30                                                       
CONECT   20   31   47                                                       
CONECT   21   32   56                                                       
CONECT   22   33   57                                                       
CONECT   23    1    2   13                                                  
CONECT   24    3   14   35                                                  
CONECT   25    4   48   56                                                  
CONECT   26    5   49   58                                                  
CONECT   27    6   50   59                                                  
CONECT   28   15   29   45                                                  
CONECT   29   19   28   44                                                  
CONECT   30   19   41   51                                                  
CONECT   31   20   35   60                                                  
CONECT   32   21   36   61                                                  
CONECT   33   22   40   58                                                  
CONECT   34   16   44   62                                                  
CONECT   35   24   31   46                                                  
CONECT   36   32   37   52                                                  
CONECT   37   36   38   53                                                  
CONECT   38   37   43   54                                                  
CONECT   39   40   42   55                                                  
CONECT   40   33   39   59                                                  
CONECT   41   30   45   47                                                  
CONECT   42   39   57   62                                                  
CONECT   43   38   60   61                                                  
CONECT   44    7    8   29   34                                             
CONECT   45    9   17   28   41                                             
CONECT   46   10   18   35   47                                             
CONECT   47   11   20   41   46                                             
CONECT   48   25                                                            
CONECT   49   26                                                            
CONECT   50   27                                                            
CONECT   51   30                                                            
CONECT   52   36                                                            
CONECT   53   37                                                            
CONECT   54   38                                                            
CONECT   55   39                                                            
CONECT   56   21   25                                                       
CONECT   57   22   42                                                       
CONECT   58   26   33                                                       
CONECT   59   27   40                                                       
CONECT   60   31   43                                                       
CONECT   61   32   43                                                       
CONECT   62   34   42                                                       
MASTER        0    0    0    0    0    0    0    0   62    0  134    0
END

View in JSmol

Synonyms

Value	Source
{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]-3,4,5-trihydroxyoxan-2-yl}methyl acetic acid	Generator

Chemical Formula

C₄₇H₇₄O₁₅

Average Mass

879.0815 Da

Monoisotopic Mass

878.50277 Da

IUPAC Name

{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]-3,4,5-trihydroxyoxan-2-yl}methyl acetate

Traditional Name

CAS Registry Number

138995-53-6

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(O)C(O)C1O

InChI Identifier

InChI=1S/C47H74O15/c1-23(2)13-12-14-24(3)35-31(60-43-38(54)37(53)36(52)32(61-43)21-56-25(4)48)20-47(11)41-30(51)19-29-28(45(41,9)17-18-46(35,47)10)15-16-34(44(29,7)8)62-42-39(55)40(59-27(6)50)33(22-57-42)58-26(5)49/h13,19,24,28,30-43,51-55H,12,14-18,20-22H2,1-11H3

InChI Key

HZVGDAABVDIGIT-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	4.17	ALOGPS
logP	3.7	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	11.97	ChemAxon
pKa (Strongest Basic)	-0.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	216.97 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	224.16 m³·mol⁻¹	ChemAxon
Polarizability	96.23 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

HMDB0034604

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013120

KNApSAcK ID

C00023928

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

131751590

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Hebevinoside XIV (NP0048020)

MOL for NP0048020 (Hebevinoside XIV)

3D MOL for NP0048020 (Hebevinoside XIV)

3D SDF for NP0048020 (Hebevinoside XIV)

3D-SDF for NP0048020 (Hebevinoside XIV)

PDB for NP0048020 (Hebevinoside XIV)

3D PDB for NP0048020 (Hebevinoside XIV)

SMILES for NP0048020 (Hebevinoside XIV)

INCHI for NP0048020 (Hebevinoside XIV)

Structure for NP0048020 (Hebevinoside XIV)

3D Structure for NP0048020 (Hebevinoside XIV)