NP-MRD: Showing NP-Card for Cynaratriol (NP0048096)

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Record Information

Version

2.0

Created at

2022-03-17 20:51:01 UTC

Updated at

2022-03-17 20:51:01 UTC

NP-MRD ID

NP0048096

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cynaratriol

Description

Cynaratriol, also known as tipropidil, belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Cynaratriol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cynaratriol has been detected, but not quantified in, several different foods, such as cardoons, globe artichokes, green vegetables, and herbs and spices. This could make cynaratriol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308102D          

 20 22  0  0  0  0            999 V2000
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384    0.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2240    0.7032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3466    0.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  1  2  0  0  0  0
  7  3  1  0  0  0  0
  8  2  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16  6  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048096

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(O)CC2C1C1OC(=O)C(O)(CO)C1CCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-7-3-4-10-13(20-14(18)15(10,19)6-16)12-8(2)11(17)5-9(7)12/h8-13,16-17,19H,1,3-6H2,2H3

> <INCHI_KEY>
OHBHGGYGWZIWCX-UHFFFAOYSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.3322

> <EXACT_MASS>
282.146723814

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.54307389395067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,8-dihydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
-0.01415802566666749

> <ALOGPS_LOGS>
-1.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.644242028020482

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.361840983359809

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8316259821793404

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
71.0589

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8-dihydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-octahydro-3aH-azuleno[4,5-b]furan-2-one

> <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       8.665   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.378   0.109   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.418   1.313   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.380  -2.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.766  -2.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.514   1.829   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    4    7                                                       
CONECT    4    3   10                                                       
CONECT    5    9   11                                                       
CONECT    6   15   16                                                       
CONECT    7    1    3    9                                                  
CONECT    8    2   11   12                                                  
CONECT    9    5    7   12                                                  
CONECT   10    4   13   15                                                  
CONECT   11    5    8   17                                                  
CONECT   12    8    9   13                                                  
CONECT   13   10   12   20                                                  
CONECT   14   15   18   20                                                  
CONECT   15    6   10   14   19                                             
CONECT   16    6                                                            
CONECT   17   11                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
3,11,13-Trihydroxy-10(14)-guaien-12,6-olide	HMDB
Tipropidil	HMDB

Chemical Formula

C₁₅H₂₂O₅

Average Mass

282.3322 Da

Monoisotopic Mass

282.14672 Da

IUPAC Name

3,8-dihydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2-one

Traditional Name

3,8-dihydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-octahydro-3aH-azuleno[4,5-b]furan-2-one

CAS Registry Number

70894-20-1

SMILES

CC1C(O)CC2C1C1OC(=O)C(O)(CO)C1CCC2=C

InChI Identifier

InChI=1S/C15H22O5/c1-7-3-4-10-13(20-14(18)15(10,19)6-16)12-8(2)11(17)5-9(7)12/h8-13,16-17,19H,1,3-6H2,2H3

InChI Key

OHBHGGYGWZIWCX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cynara cardunculus	FooDB	KNAPSACK
Cynara scolymus	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

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	0.24	ALOGPS
logP	-0.014	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	11.36	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.06 m³·mol⁻¹	ChemAxon
Polarizability	29.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034983

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013584

KNApSAcK ID

C00020855

Chemspider ID

26503332

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14138149

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cynaratriol (NP0048096)

MOL for NP0048096 (Cynaratriol)

3D MOL for NP0048096 (Cynaratriol)

3D SDF for NP0048096 (Cynaratriol)

3D-SDF for NP0048096 (Cynaratriol)

PDB for NP0048096 (Cynaratriol)

3D PDB for NP0048096 (Cynaratriol)

SMILES for NP0048096 (Cynaratriol)

INCHI for NP0048096 (Cynaratriol)

Structure for NP0048096 (Cynaratriol)

3D Structure for NP0048096 (Cynaratriol)