NP-MRD: Showing NP-Card for Ranunculin (NP0050665)

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Record Information

Version

2.0

Created at

2022-04-27 22:01:16 UTC

Updated at

2022-04-27 22:01:16 UTC

NP-MRD ID

NP0050665

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ranunculin

Description

Ranunculin belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Ranunculin is an extremely weak basic (essentially neutral) compound (based on its pKa). On maceration, for example when the plant is wounded, it is enzymatically broken down into glucose and the toxin protoanemonin. Ranunculin is an instable glucoside found in plants of the buttercup family (Ranunculaceae). Ranunculin is a potentially toxic compound. Ranunculin (RAN) inhibited the incorporation of 3H-labeled precursors into DNA and RNA of L1210 cells. In the meantime, SOD and CAT were shown to partly revoke the inhibitory effects of RAN upon the incorporation of 3H-TdR into DNA. The cytotoxicity of RAN in vitro may be due to inhibition of DNA polymerase and increase of oxygen free radicals. Ranunculin is found in Pulsatilla chinensis , Anemone coronaria, Anemone nemorosa, Anemone occidentalis, Anemone patens, Anemone ranunculoides, Anemone spp., Caltha palustris L. , Clematis alpina, Clematis flammula , Clematis recta , Clematis spp., Clematis vitalba , Pulsatilla pratensis, Pulsatilla vulgaris , Ranunculus acris , Ranunculus bulbosus , Ranunculus multifidus , Ranunculus pinguis, Ranunculus sceleratus , Ranunculus spp. and Trollius europaeus. RAN (15 mumol/L) markedly decreased DNA synthesis catalyzed by DNA polymerase I and promoted the generation of superoxide anions in DMSO/KO2 system.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08291401002D          

 25 26  0  0  1  0            999 V2000
   -0.6674    4.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    3.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    8.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.7036    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000    8.0036    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4125    3.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.4161    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    8.0036    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    7.1786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    6.7661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    9.2411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974    2.7666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    9.2411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    8.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.7661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.9411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674    4.2187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    7.1786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7351    5.0781    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    8.8286    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.8286    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.5911    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.5911    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    6.3536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  5  1  1  0  0  0  0
  5  4  1  1  0  0  0
  6  3  1  1  0  0  0
  7  2  1  0  0  0  0
  8  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  3  1  0  0  0  0
 13  7  2  0  0  0  0
  8 14  1  6  0  0  0
  9 15  1  6  0  0  0
 10 16  1  6  0  0  0
 17  4  1  0  0  0  0
 11 17  1  1  0  0  0
 18  5  1  0  0  0  0
 18  7  1  0  0  0  0
 19  6  1  0  0  0  0
 19 11  1  0  0  0  0
  5 20  1  6  0  0  0
  6 21  1  6  0  0  0
  8 22  1  1  0  0  0
  9 23  1  6  0  0  0
 10 24  1  1  0  0  0
 11 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050665

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CO[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H16O8/c12-3-6-8(14)9(15)10(16)11(19-6)17-4-5-1-2-7(13)18-5/h1-2,5-6,8-12,14-16H,3-4H2/t5-,6+,8+,9-,10+,11+/m0/s1

> <INCHI_KEY>
TYWXNGXVSZRXNA-NVZSGMJQSA-N

> <FORMULA>
C11H16O8

> <MOLECULAR_WEIGHT>
276.2399

> <EXACT_MASS>
276.084517488

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.33770334296856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
-2.15

> <JCHEM_LOGP>
-1.8645549989999997

> <ALOGPS_LOGS>
-0.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.213455353482614

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.680057856271231

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810834237218566

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
59.623200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ranunculin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0      -1.246   7.875   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770   6.410   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  15.710   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  10.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   8.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000  14.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.770   6.410   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  15.710   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  14.940   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  13.400   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  12.630   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  17.250   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.675   5.164   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334  17.250   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.001  15.710   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -4.001  12.630   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334  11.090   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.246   7.875   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.000  13.400   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       1.372   9.479   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.000  16.480   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.667  16.480   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.334  14.170   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.001  14.170   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.667  11.860   0.000  0.00  0.00           H+0
CONECT    1    2    5                                                       
CONECT    2    1    7                                                       
CONECT    3    6   12                                                       
CONECT    4    5   17                                                       
CONECT    5    1    4   18   20                                             
CONECT    6    3    8   19   21                                             
CONECT    7    2   13   18                                                  
CONECT    8    6    9   14   22                                             
CONECT    9    8   10   15   23                                             
CONECT   10    9   11   16   24                                             
CONECT   11   10   17   19   25                                             
CONECT   12    3                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17    4   11                                                       
CONECT   18    5    7                                                       
CONECT   19    6   11                                                       
CONECT   20    5                                                            
CONECT   21    6                                                            
CONECT   22    8                                                            
CONECT   23    9                                                            
CONECT   24   10                                                            
CONECT   25   11                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
((2S)-5-oxo-2,5-Dihydro-2-furanyl)methyl beta-D-glucopyranoside	MeSH

Chemical Formula

C₁₁H₁₆O₈

Average Mass

276.2399 Da

Monoisotopic Mass

276.08452 Da

IUPAC Name

(5S)-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,5-dihydrofuran-2-one

Traditional Name

ranunculin

CAS Registry Number

Not Available

SMILES

[H][C@]1(CO[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)OC(=O)C=C1

InChI Identifier

InChI=1S/C11H16O8/c12-3-6-8(14)9(15)10(16)11(19-6)17-4-5-1-2-7(13)18-5/h1-2,5-6,8-12,14-16H,3-4H2/t5-,6+,8+,9-,10+,11+/m0/s1

InChI Key

TYWXNGXVSZRXNA-NVZSGMJQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anemone chinensis	Plant	KNApSAcK
Anemone coronaria	Plant	KNApSAcK
Anemone nemorosa	Plant	KNApSAcK
Anemone occidentalis	Plant	KNApSAcK
Anemone patens	Plant	KNApSAcK
Anemone ranunculoides	Plant	KNApSAcK
Anemone spp.	Plant	KNApSAcK
Caltha palustris	Plant	KNApSAcK
Clematis alpina	Plant	KNApSAcK
Clematis flammula	Plant	KNApSAcK
Clematis recta	Plant	KNApSAcK
Clematis spp.	Plant	KNApSAcK
Clematis vitalba	Plant	KNApSAcK
Pulsatilla pratensis	Plant	KNApSAcK
Pulsatilla vulgaris	Plant	KNApSAcK
Ranunculus acris	Plant	KNApSAcK
Ranunculus bulbosus	Plant	KNApSAcK
Ranunculus multifidus	Plant	KNApSAcK
Ranunculus pinguis	LOTUS Database	35616633
Ranunculus sceleratus	Plant	KNApSAcK
Ranunculus spp.	Plant	KNApSAcK
Trollius europaeus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
2-furanone
Monosaccharide
Oxane
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glycoside (CHEBI:8778 )
Cyanogenic glucosides (C08512 )
Phytotoxins (C08512 )

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	-2.2	ALOGPS
logP	-1.9	ChemAxon
logS	-0.2	ALOGPS
pKa (Strongest Acidic)	5.68	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.62 m³·mol⁻¹	ChemAxon
Polarizability	25.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001322

Chemspider ID

Not Available

KEGG Compound ID

C08512

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ranunculin

METLIN ID

Not Available

PubChem Compound

441581

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ranunculin (NP0050665)

MOL for NP0050665 (Ranunculin)

3D MOL for NP0050665 (Ranunculin)

3D SDF for NP0050665 (Ranunculin)

3D-SDF for NP0050665 (Ranunculin)

PDB for NP0050665 (Ranunculin)

3D PDB for NP0050665 (Ranunculin)

SMILES for NP0050665 (Ranunculin)

INCHI for NP0050665 (Ranunculin)

Structure for NP0050665 (Ranunculin)

3D Structure for NP0050665 (Ranunculin)