NP-MRD: Showing NP-Card for Cyclocalopin C1 (NP0049497)

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Record Information

Version

2.0

Created at

2022-03-17 21:13:28 UTC

Updated at

2022-03-17 21:13:28 UTC

NP-MRD ID

NP0049497

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyclocalopin C1

Description

Cyclocalopin C1 belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Cyclocalopin C1 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cyclocalopin C1 has been detected, but not quantified in, mushrooms. This could make cyclocalopin C1 a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241211412D          

 21 23  0  0  0  0            999 V2000
   -2.0510   -0.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0510   -1.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373   -1.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -1.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -0.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373    0.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587   -1.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414   -0.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1587   -0.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9701    0.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2410    0.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992    1.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1134    1.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3844    0.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373    0.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373   -2.3267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4390   -0.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2245   -1.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7676   -0.0700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0510    1.0781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9687    2.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 16  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 19  1  0  0  0  0
 11 12  1  0  0  0  0
 11 20  1  0  0  0  0
 12 13  1  0  0  0  0
 12 21  2  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049497

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1COC(=O)C2OC(C)(O)C3(C=CC(=C)C(O)C3O)C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O6/c1-7-4-5-15(12(17)10(7)16)9-8(2)6-20-13(18)11(9)21-14(15,3)19/h4-5,8-12,16-17,19H,1,6H2,2-3H3

> <INCHI_KEY>
JCKVAXRAVFAUJA-UHFFFAOYSA-N

> <FORMULA>
C15H20O6

> <MOLECULAR_WEIGHT>
296.3157

> <EXACT_MASS>
296.125988372

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.39019405437039

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2',5,6-trihydroxy-2',4'-dimethyl-4-methylidene-2',3'a,4',5',7',7'a-hexahydrospiro[cyclohexane-1,3'-furo[2,3-c]pyra]-2-en-7'-one

> <ALOGPS_LOGP>
-0.13

> <JCHEM_LOGP>
-0.45296970933333325

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.265960971837941

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.678611573285723

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4310730480724017

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
73.452

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2',5,6-trihydroxy-2',4'-dimethyl-4-methylidene-3'a,4',5',7'a-tetrahydrospiro[cyclohexane-1,3'-furo[2,3-c]pyra]-2-en-7'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.829  -0.493   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.829  -2.033   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.496  -2.803   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.167  -2.033   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.167  -0.493   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.496   0.275   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.296  -2.508   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.197  -1.263   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.296  -0.023   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.811   0.267   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.317   1.723   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.305   2.888   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.212   2.593   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.718   1.132   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.496   1.815   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.496  -4.343   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.686  -0.865   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.286  -2.351   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.300  -0.131   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.829   2.012   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.808   4.343   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    1    5   15                                                  
CONECT    7    4    8                                                       
CONECT    8    7    9   17   18                                             
CONECT    9    5    8   10   14                                             
CONECT   10    9   11   19                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14    9   13                                                       
CONECT   15    6                                                            
CONECT   16    3                                                            
CONECT   17    8                                                            
CONECT   18    8                                                            
CONECT   19   10                                                            
CONECT   20   11                                                            
CONECT   21   12                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₆

Average Mass

296.3157 Da

Monoisotopic Mass

296.12599 Da

IUPAC Name

2',5,6-trihydroxy-2',4'-dimethyl-4-methylidene-2',3'a,4',5',7',7'a-hexahydrospiro[cyclohexane-1,3'-furo[2,3-c]pyra]-2-en-7'-one

Traditional Name

2',5,6-trihydroxy-2',4'-dimethyl-4-methylidene-3'a,4',5',7'a-tetrahydrospiro[cyclohexane-1,3'-furo[2,3-c]pyra]-2-en-7'-one

CAS Registry Number

Not Available

SMILES

CC1COC(=O)C2OC(C)(O)C3(C=CC(=C)C(O)C3O)C12

InChI Identifier

InChI=1S/C15H20O6/c1-7-4-5-15(12(17)10(7)16)9-8(2)6-20-13(18)11(9)21-14(15,3)19/h4-5,8-12,16-17,19H,1,6H2,2-3H3

InChI Key

JCKVAXRAVFAUJA-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...
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 furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Furopyran
Delta valerolactone
Delta_valerolactone
Oxane
Pyran
Furan
Tetrahydrofuran
1,2-diol
Carboxylic acid ester
Hemiacetal
Lactone
Secondary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
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	-0.13	ALOGPS
logP	-0.45	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	11.68	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.45 m³·mol⁻¹	ChemAxon
Polarizability	29.39 Å³	ChemAxon
Number of Rings	3	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

HMDB0039812

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019462

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

85398159

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cyclocalopin C1 (NP0049497)

MOL for NP0049497 (Cyclocalopin C1)

3D MOL for NP0049497 (Cyclocalopin C1)

3D SDF for NP0049497 (Cyclocalopin C1)

3D-SDF for NP0049497 (Cyclocalopin C1)

PDB for NP0049497 (Cyclocalopin C1)

3D PDB for NP0049497 (Cyclocalopin C1)

SMILES for NP0049497 (Cyclocalopin C1)

INCHI for NP0049497 (Cyclocalopin C1)

Structure for NP0049497 (Cyclocalopin C1)

3D Structure for NP0049497 (Cyclocalopin C1)