NP-MRD: Showing NP-Card for Umbelliferose (NP0337766)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 12:20:58 UTC

Updated at

2024-09-11 12:20:59 UTC

NP-MRD ID

NP0337766

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Umbelliferose

Description

Umbelliferose was first documented in 2016 (PMID: 26612497). Based on a literature review very few articles have been published on Umbelliferose (PMID: 35807345).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262314532D          

 34 36  0  0  0  0            999 V2000
   -1.5399    6.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7920    7.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    1.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0938    4.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850    5.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2400    6.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2333    2.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    5.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330    6.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583    2.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5821    4.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8810    6.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7751    4.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359    5.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132    3.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2231    4.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429    5.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458    3.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3469    6.8842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5990    7.0812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0839    1.1536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868    4.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6440    5.4865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1781    7.5958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5432    1.9072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1341    3.9172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0740    6.3696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202    3.5742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0979    3.6142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4780    5.7565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4949    5.8550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839    4.8004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    3.3593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1978    4.4573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  4  1  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  0  0  0  0
 20  2  1  0  0  0  0
 21  3  1  0  0  0  0
 22  4  1  0  0  0  0
 23  8  1  0  0  0  0
 24  9  1  0  0  0  0
 25 10  1  0  0  0  0
 26 11  1  0  0  0  0
 27 12  1  0  0  0  0
 28 13  1  0  0  0  0
 29 15  1  0  0  0  0
 30  5  1  0  0  0  0
 30 16  1  0  0  0  0
 31  6  1  0  0  0  0
 31 17  1  0  0  0  0
 32 14  1  0  0  0  0
 32 16  1  0  0  0  0
 33  7  1  0  0  0  0
 33 18  1  0  0  0  0
 34 17  1  0  0  0  0
 34 18  1  0  0  0  0
M  END


  Mrv2104 05262314532D          

 34 36  0  0  0  0            999 V2000
   -1.5399    6.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7920    7.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    1.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0938    4.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2850    5.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2400    6.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2333    2.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    5.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330    6.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583    2.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5821    4.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8810    6.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7751    4.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359    5.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132    3.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2231    4.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429    5.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458    3.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3469    6.8842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5990    7.0812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0839    1.1536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868    4.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6440    5.4865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1781    7.5958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5432    1.9072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1341    3.9172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0740    6.3696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202    3.5742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0979    3.6142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4780    5.7565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4949    5.8550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839    4.8004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    3.3593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1978    4.4573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  4  1  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  0  0  0  0
 20  2  1  0  0  0  0
 21  3  1  0  0  0  0
 22  4  1  0  0  0  0
 23  8  1  0  0  0  0
 24  9  1  0  0  0  0
 25 10  1  0  0  0  0
 26 11  1  0  0  0  0
 27 12  1  0  0  0  0
 28 13  1  0  0  0  0
 29 15  1  0  0  0  0
 30  5  1  0  0  0  0
 30 16  1  0  0  0  0
 31  6  1  0  0  0  0
 31 17  1  0  0  0  0
 32 14  1  0  0  0  0
 32 16  1  0  0  0  0
 33  7  1  0  0  0  0
 33 18  1  0  0  0  0
 34 17  1  0  0  0  0
 34 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337766

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2OC2OC(CO)C(O)C(O)C2O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1/C18H32O16/c19-1-5-8(23)11(26)13(28)16(30-5)32-14-12(27)9(24)6(2-20)31-17(14)34-18(4-22)15(29)10(25)7(3-21)33-18/h5-17,19-29H,1-4H2

> <INCHI_KEY>
LNRUEZIDUKQGRH-UHFFFAOYNA-N

> <FORMULA>
C18H32O16

> <MOLECULAR_WEIGHT>
504.438

> <EXACT_MASS>
504.16903495

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.271561894225

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
-6.299670609333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.281794008304352

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.78919144330635

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4558261942643216

> <JCHEM_POLAR_SURFACE_AREA>
268.67999999999995

> <JCHEM_REFRACTIVITY>
101.18740000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -2.874  12.530   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.212  13.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.397   3.560   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.042   8.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.399  11.066   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.181  12.394   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.302   4.806   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.429   9.921   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.675  12.714   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.842   4.806   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.953   8.457   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.645  11.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.447   8.136   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.120  10.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.318   6.271   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.416   9.281   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.627   9.785   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.072   7.176   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.381  12.851   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.718  13.218   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.023   2.153   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.535   8.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.935  10.241   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.199  14.179   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.747   3.560   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.984   7.312   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.138  11.890   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.971   6.672   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.783   6.747   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.892  10.745   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.657  10.929   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.090   8.961   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.826   6.271   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.103   8.320   0.000  0.00  0.00           O+0
CONECT    1    5   19                                                       
CONECT    2    6   20                                                       
CONECT    3    7   21                                                       
CONECT    4   18   22                                                       
CONECT    5    1    8   30                                                  
CONECT    6    2    9   31                                                  
CONECT    7    3   10   33                                                  
CONECT    8    5   11   23                                                  
CONECT    9    6   12   24                                                  
CONECT   10    7   15   25                                                  
CONECT   11    8   13   26                                                  
CONECT   12    9   14   27                                                  
CONECT   13   11   16   28                                                  
CONECT   14   12   17   32                                                  
CONECT   15   10   18   29                                                  
CONECT   16   13   30   32                                                  
CONECT   17   14   31   34                                                  
CONECT   18    4   15   33   34                                             
CONECT   19    1                                                            
CONECT   20    2                                                            
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    8                                                            
CONECT   24    9                                                            
CONECT   25   10                                                            
CONECT   26   11                                                            
CONECT   27   12                                                            
CONECT   28   13                                                            
CONECT   29   15                                                            
CONECT   30    5   16                                                       
CONECT   31    6   17                                                       
CONECT   32   14   16                                                       
CONECT   33    7   18                                                       
CONECT   34   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₃₂O₁₆

Average Mass

504.4380 Da

Monoisotopic Mass

504.16903 Da

IUPAC Name

2-[(2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-[(2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2OC2OC(CO)C(O)C(O)C2O)C(O)C1O

InChI Identifier

InChI=1/C18H32O16/c19-1-5-8(23)11(26)13(28)16(30-5)32-14-12(27)9(24)6(2-20)31-17(14)34-18(4-22)15(29)10(25)7(3-21)33-18/h5-17,19-29H,1-4H2

InChI Key

LNRUEZIDUKQGRH-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	-6.3	ChemAxon
pKa (Strongest Acidic)	11.79	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	268.68 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	101.19 m³·mol⁻¹	ChemAxon
Polarizability	46.27 Å³	ChemAxon
Number of Rings	3	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Panneerselvam C, Murugan K, Roni M, Aziz AT, Suresh U, Rajaganesh R, Madhiyazhagan P, Subramaniam J, Dinesh D, Nicoletti M, Higuchi A, Alarfaj AA, Munusamy MA, Kumar S, Desneux N, Benelli G: Fern-synthesized nanoparticles in the fight against malaria: LC/MS analysis of Pteridium aquilinum leaf extract and biosynthesis of silver nanoparticles with high mosquitocidal and antiplasmodial activity. Parasitol Res. 2016 Mar;115(3):997-1013. doi: 10.1007/s00436-015-4828-x. Epub 2015 Nov 27. [PubMed:26612497 ]
Ishida M, Ohara R, Miyagawa F, Kikuzaki H, Nishi K, Onda H, Yoshino N, Sugahara T: Umbelliferose Isolated from Cuminum cyminum L. Seeds Inhibits Antigen-Induced Degranulation in Rat Basophilic Leukemia RBL-2H3 Cells. Molecules. 2022 Jun 25;27(13):4101. doi: 10.3390/molecules27134101. [PubMed:35807345 ]

Showing NP-Card for Umbelliferose (NP0337766)

MOL for NP0337766 (Umbelliferose)

3D MOL for NP0337766 (Umbelliferose)

3D SDF for NP0337766 (Umbelliferose)

3D-SDF for NP0337766 (Umbelliferose)

PDB for NP0337766 (Umbelliferose)

3D PDB for NP0337766 (Umbelliferose)

SMILES for NP0337766 (Umbelliferose)

INCHI for NP0337766 (Umbelliferose)

Structure for NP0337766 (Umbelliferose)

3D Structure for NP0337766 (Umbelliferose)