NP-MRD: Showing NP-Card for Cardozin (NP0074148)

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Record Information

Version

2.0

Created at

2022-04-28 19:18:56 UTC

Updated at

2022-04-28 19:18:56 UTC

NP-MRD ID

NP0074148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cardozin

Description

N-butyl-beta-d-fructopyranoside belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. Cardozin is found in Actinidia chinensis, Aesculus chinensis, Cynomorium songaricum, Diospyros kaki, Machilus zuihoensis, Opuntia ficus-indica, Opuntia ficus-indica var.saboten , Pileostegia viburnoides var. glabrescens, Sparganium eurycarpum, Sparganium stoloniferum and Syzygium levinei. Cardozin was first documented in 2003 (PMID: 15015352). Based on a literature review a significant number of articles have been published on n-butyl-beta-d-fructopyranoside (PMID: 17225537) (PMID: 20422359) (PMID: 19475996) (PMID: 30452165) (PMID: 19023813) (PMID: 16758994).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    4.3311    0.3144    1.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8932    0.2011   -0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5066    0.8482   -0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5289    0.1196    0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912    0.4497    0.7257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7605    0.5643   -0.0107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6196    1.7768   -0.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7722    1.9203   -1.7362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8074    0.9842    0.8517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511    0.5281    0.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2038   -0.9744    0.6344 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2905   -1.3923   -0.1553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9438   -1.5929    0.0833 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1790   -2.7902   -0.5780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2895   -0.5645   -0.8089 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3625   -1.2303   -1.5870 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9614    1.2305    1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4379    0.2718    1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9670   -0.5491    2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6264    0.6030   -0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360   -0.8792   -0.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6352    1.9134    0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2703    0.7891   -1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9878    0.3177    1.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7568   -1.0088    0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3870    2.7011   -0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2011    1.6323   -1.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8492    2.8921   -1.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7776    1.0368    1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3914    0.8571   -0.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749   -1.2760    1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0118   -2.1641   -0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2597   -1.7385    0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7031   -3.5362   -0.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0554   -0.1921   -1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0409   -2.0629   -1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  6  5  1  1
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 13 33  1  1
 14 34  1  0
 15 35  1  6
 16 36  1  0
M  END


  Mrv1652304282221182D          

 16 16  0  0  1  0            999 V2000
   -2.4133    2.7232    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9762    3.4228    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1517    3.3940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7643    2.6656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2015    1.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0260    1.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0228    3.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0347    3.8502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499    2.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646    2.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3791    2.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0935    2.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8080    2.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.0936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635    4.1512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2378    2.7519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  1  0  0  0
  7  8  1  0  0  0  0
  4  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 14  1  6  0  0  0
  2 15  1  1  0  0  0
  1 16  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0074148

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCO[C@]1(CO)OC[C@@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O6/c1-2-3-4-15-10(6-11)9(14)8(13)7(12)5-16-10/h7-9,11-14H,2-6H2,1H3/t7-,8-,9+,10-/m1/s1

> <INCHI_KEY>
NAJPAGUETSZHOG-DOLQZWNJSA-N

> <FORMULA>
C10H20O6

> <MOLECULAR_WEIGHT>
236.264

> <EXACT_MASS>
236.125988364

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.237343070113827

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R)-2-butoxy-2-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.85

> <JCHEM_LOGP>
-0.7909737996666667

> <ALOGPS_LOGS>
0.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.174320462324012

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.070467119002501

> <JCHEM_PKA_STRONGEST_BASIC>
-3.453646879727371

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
54.98559999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.89e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5R)-2-butoxy-2-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -4.505   5.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.689   6.389   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.150   6.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.427   4.976   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.243   3.670   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.782   3.723   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.043   5.651   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.065   7.187   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.093   4.206   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.241   4.976   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.574   4.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.908   4.976   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.242   4.206   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334   7.641   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.412   7.749   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -6.044   5.137   0.000  0.00  0.00           O+0
CONECT    1    2    6   16                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5    7    9                                             
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    3                                                            
CONECT   15    2                                                            
CONECT   16    1                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
N-Butyl-b-D-fructopyranoside	Generator
N-Butyl-β-D-fructopyranoside	Generator
N-Butyl fructopyranoside	MeSH

Chemical Formula

C₁₀H₂₀O₆

Average Mass

236.2640 Da

Monoisotopic Mass

236.12599 Da

IUPAC Name

(2R,3S,4R,5R)-2-butoxy-2-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3S,4R,5R)-2-butoxy-2-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CCCCO[C@]1(CO)OC[C@@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C10H20O6/c1-2-3-4-15-10(6-11)9(14)8(13)7(12)5-16-10/h7-9,11-14H,2-6H2,1H3/t7-,8-,9+,10-/m1/s1

InChI Key

NAJPAGUETSZHOG-DOLQZWNJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actinidia chinensis	LOTUS Database	35616633
Aesculus chinensis	LOTUS Database	35616633
Cynomorium songaricum	LOTUS Database	35616633
Diospyros kaki	LOTUS Database	35616633
Machilus zuihoensis	LOTUS Database	35616633
Opuntia ficus-indica	LOTUS Database	35616633
Opuntia ficus-indica var.saboten	Plant	KNApSAcK
Pileostegia viburnoides var. glabrescens	Plant	KNApSAcK
Sparganium eurycarpum	LOTUS Database	35616633
Sparganium stoloniferum	Plant	KNApSAcK
Syzygium levinei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Oxane
Monosaccharide
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-0.85	ALOGPS
logP	-0.79	ChemAxon
logS	0.09	ALOGPS
pKa (Strongest Acidic)	12.07	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	54.99 m³·mol⁻¹	ChemAxon
Polarizability	24.24 Å³	ChemAxon
Number of Rings	1	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

C00035133

Chemspider ID

62840006

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50914217

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhu JJ, Zhang CF, Zhang M, Wang ZT: [Studies on chemical constituents in roots of Rumex dentatus]. Zhongguo Zhong Yao Za Zhi. 2006 Oct;31(20):1691-3. [PubMed:17225537 ]
Lee SY, Choi SU, Lee JH, Lee DU, Lee KR: A new phenylpropane glycoside from the rhizome of Sparganium stoloniferum. Arch Pharm Res. 2010 Apr;33(4):515-21. doi: 10.1007/s12272-010-0404-1. Epub 2010 Apr 27. [PubMed:20422359 ]
Liu Z, Ji S, Zhang Y, Meng D, Li X: Myricarborin A and n-butyl-alpha-L-rhamnopyranoside, two novel compounds from the bark of Myrica rubra. Nat Prod Commun. 2009 Apr;4(4):513-6. [PubMed:19475996 ]
Chen SH, Yu J, Lia QW, Zhao JP, Wedge DE, Duke SO, Liao DF, Wang YH, Fronczek FR, Khan IA, Wanga W: 7alpha-Hydroxyfriedelan-3-one-26-ol-29-oic acid and other Constituents from Pileostegia viburnoides var. glabrescens. Nat Prod Commun. 2016 Jul;11(7):931-934. [PubMed:30452165 ]
Sayed HM, Mohamed MH, Farag SF, Mohamed GA, Omobuwajo OR, Proksch P: Fructose-amino acid conjugate and other constituents from Cyperus rotundus L. Nat Prod Res. 2008;22(17):1487-97. doi: 10.1080/14786410802038556. [PubMed:19023813 ]
An N, Lin J, Yang SL, Zou ZM, Xu LZ: A new glycoside from Alpinia officinarum. Yao Xue Xue Bao. 2006 Mar;41(3):233-5. [PubMed:16758994 ]
Zeng JW, Qian SH, Wu JZ, Yang NY: [Studies on involatile constituents of Mentha haplocalyx]. Zhongguo Zhong Yao Za Zhi. 2006 Mar;31(5):400-2. [PubMed:16711426 ]
Xu J, Li X, Zhang P, Li ZL, Wang Y: Antiinflammatory constituents from the roots of Smilax bockii warb. Arch Pharm Res. 2005 Apr;28(4):395-9. doi: 10.1007/BF02977667. [PubMed:15918511 ]
Wang T, Cui SY, Suo YR, Lu RH: [Studies on water-soluble chemical constituents in root of Achyranthes bidentata]. Zhongguo Zhong Yao Za Zhi. 2004 Jul;29(7):649-52. [PubMed:15503770 ]
Deng YR, He L, Li WQ, Wang HQ: [Studies on chemical constituents in herb of Lamium maculatum L. var Kansuense]. Zhongguo Zhong Yao Za Zhi. 2003 Aug;28(8):730-2. [PubMed:15015352 ]
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Showing NP-Card for Cardozin (NP0074148)

MOL for NP0074148 (Cardozin)

3D MOL for NP0074148 (Cardozin)

3D SDF for NP0074148 (Cardozin)

3D-SDF for NP0074148 (Cardozin)

PDB for NP0074148 (Cardozin)

3D PDB for NP0074148 (Cardozin)

SMILES for NP0074148 (Cardozin)

INCHI for NP0074148 (Cardozin)

Structure for NP0074148 (Cardozin)

3D Structure for NP0074148 (Cardozin)