NP-MRD: Showing NP-Card for Cyclocalopin B (NP0049496)

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Record Information

Version

2.0

Created at

2022-03-17 21:13:27 UTC

Updated at

2022-03-17 21:13:28 UTC

NP-MRD ID

NP0049496

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyclocalopin B

Description

Cyclocalopin B 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 B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cyclocalopin B has been detected, but not quantified in, mushrooms. Cyclocalopin B is found in Boletus coniferarum. This could make cyclocalopin b a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061311252D          

 27 29  0  0  0  0            999 V2000
    1.0751   -0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4244    0.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6957    0.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0971   -3.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375   -1.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4342   -1.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0329   -0.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7718   -0.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2195   -0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8403    1.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9647    0.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9322   -1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5028   -0.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583   -1.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1995   -0.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2717   -1.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173   -2.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1652   -1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1093    0.6684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2680    0.9915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7978   -2.3106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3930   -2.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5590   -0.9017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5370    0.6090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9305   -0.2746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0165   -2.5096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  1  1  0  0  0  0
  9  6  2  0  0  0  0
 10  2  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13 10  1  0  0  0  0
 14  9  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18  5  1  0  0  0  0
 19  7  1  0  0  0  0
 19 13  1  0  0  0  0
 19 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20 11  2  0  0  0  0
 21 12  2  0  0  0  0
 22 17  2  0  0  0  0
 23 18  1  0  0  0  0
 24  8  1  0  0  0  0
 24 17  1  0  0  0  0
 25 11  1  0  0  0  0
 25 14  1  0  0  0  0
 26 12  1  0  0  0  0
 26 16  1  0  0  0  0
 27 15  1  0  0  0  0
 27 18  1  0  0  0  0
M  END


  Mrv0541 05061311252D          

 27 29  0  0  0  0            999 V2000
    1.0751   -0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4244    0.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6957    0.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0971   -3.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375   -1.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4342   -1.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0329   -0.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7718   -0.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2195   -0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8403    1.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9647    0.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9322   -1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5028   -0.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583   -1.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1995   -0.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2717   -1.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173   -2.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1652   -1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1093    0.6684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2680    0.9915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7978   -2.3106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3930   -2.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5590   -0.9017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5370    0.6090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9305   -0.2746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0165   -2.5096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  1  1  0  0  0  0
  9  6  2  0  0  0  0
 10  2  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13 10  1  0  0  0  0
 14  9  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18  5  1  0  0  0  0
 19  7  1  0  0  0  0
 19 13  1  0  0  0  0
 19 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20 11  2  0  0  0  0
 21 12  2  0  0  0  0
 22 17  2  0  0  0  0
 23 18  1  0  0  0  0
 24  8  1  0  0  0  0
 24 17  1  0  0  0  0
 25 11  1  0  0  0  0
 25 14  1  0  0  0  0
 26 12  1  0  0  0  0
 26 16  1  0  0  0  0
 27 15  1  0  0  0  0
 27 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1COC(=O)C2OC(C)(O)C3(CC=C(C)C(OC(C)=O)C3OC(C)=O)C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O8/c1-9-6-7-19(16(26-12(4)21)14(9)25-11(3)20)13-10(2)8-24-17(22)15(13)27-18(19,5)23/h6,10,13-16,23H,7-8H2,1-5H3

> <INCHI_KEY>
OAMXBKFTDLDKCN-UHFFFAOYSA-N

> <FORMULA>
C19H26O8

> <MOLECULAR_WEIGHT>
382.4049

> <EXACT_MASS>
382.162767808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.84871644627356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(acetyloxy)-2'-hydroxy-2',4,4'-trimethyl-7'-oxo-2',3'a,4',5',7',7'a-hexahydrospiro[cyclohexane-1,3'-furo[2,3-c]pyra]-3-en-5-yl acetate

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
0.7332690976666661

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.739059928713303

> <JCHEM_PKA_STRONGEST_BASIC>
-4.225135187180801

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
91.71090000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(acetyloxy)-2'-hydroxy-2',4,4'-trimethyl-7'-oxo-3'a,4',5',7'a-tetrahydrospiro[cyclohexane-1,3'-furo[2,3-c]pyra]-3-en-5-yl acetate

> <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       2.007  -0.291   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.259   0.738   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.499   3.500   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.765   1.740   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.781  -5.826   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.243  -2.654   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.544  -3.479   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.395  -0.497   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.307  -1.116   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.876  -0.754   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.435   1.961   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.401   1.026   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.340  -2.198   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.672  -0.402   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.322  -3.384   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.972  -1.227   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.841  -3.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.006  -4.302   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.908  -2.765   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.071   1.248   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.100   1.851   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.823  -4.313   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.467  -4.238   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.377  -1.683   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.736   1.137   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.337  -0.513   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       7.497  -4.685   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5   18                                                            
CONECT    6    7    9                                                       
CONECT    7    6   19                                                       
CONECT    8   10   24                                                       
CONECT    9    1    6   14                                                  
CONECT   10    2    8   13                                                  
CONECT   11    3   20   25                                                  
CONECT   12    4   21   26                                                  
CONECT   13   10   15   19                                                  
CONECT   14    9   16   25                                                  
CONECT   15   13   17   27                                                  
CONECT   16   14   19   26                                                  
CONECT   17   15   22   24                                                  
CONECT   18    5   19   23   27                                             
CONECT   19    7   13   16   18                                             
CONECT   20   11                                                            
CONECT   21   12                                                            
CONECT   22   17                                                            
CONECT   23   18                                                            
CONECT   24    8   17                                                       
CONECT   25   11   14                                                       
CONECT   26   12   16                                                       
CONECT   27   15   18                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
6-(Acetyloxy)-2'-hydroxy-2',4,4'-trimethyl-7'-oxo-2',3'a,4',5',7',7'a-hexahydrospiro[cyclohexane-1,3'-furo[2,3-c]pyra]-3-en-5-yl acetic acid	Generator

Chemical Formula

C₁₉H₂₆O₈

Average Mass

382.4049 Da

Monoisotopic Mass

382.16277 Da

IUPAC Name

6-(acetyloxy)-2'-hydroxy-2',4,4'-trimethyl-7'-oxo-2',3'a,4',5',7',7'a-hexahydrospiro[cyclohexane-1,3'-furo[2,3-c]pyra]-3-en-5-yl acetate

Traditional Name

6-(acetyloxy)-2'-hydroxy-2',4,4'-trimethyl-7'-oxo-3'a,4',5',7'a-tetrahydrospiro[cyclohexane-1,3'-furo[2,3-c]pyra]-3-en-5-yl acetate

CAS Registry Number

Not Available

SMILES

CC1COC(=O)C2OC(C)(O)C3(CC=C(C)C(OC(C)=O)C3OC(C)=O)C12

InChI Identifier

InChI=1S/C19H26O8/c1-9-6-7-19(16(26-12(4)21)14(9)25-11(3)20)13-10(2)8-24-17(22)15(13)27-18(19,5)23/h6,10,13-16,23H,7-8H2,1-5H3

InChI Key

OAMXBKFTDLDKCN-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...
Boletus coniferarum	LOTUS Database	35616633
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
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Oxane
Pyran
Furan
Tetrahydrofuran
Lactone
Hemiacetal
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	1.28	ALOGPS
logP	0.73	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	11.74	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.71 m³·mol⁻¹	ChemAxon
Polarizability	37.85 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

HMDB0039811

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019461

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

73118466

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cyclocalopin B (NP0049496)

MOL for NP0049496 (Cyclocalopin B)

3D MOL for NP0049496 (Cyclocalopin B)

3D SDF for NP0049496 (Cyclocalopin B)

3D-SDF for NP0049496 (Cyclocalopin B)

PDB for NP0049496 (Cyclocalopin B)

3D PDB for NP0049496 (Cyclocalopin B)

SMILES for NP0049496 (Cyclocalopin B)

INCHI for NP0049496 (Cyclocalopin B)

Structure for NP0049496 (Cyclocalopin B)

3D Structure for NP0049496 (Cyclocalopin B)