NP-MRD: Showing NP-Card for Cacalon (NP0061866)

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Record Information

Version

2.0

Created at

2022-04-28 06:34:01 UTC

Updated at

2022-04-28 06:34:01 UTC

NP-MRD ID

NP0061866

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cacalon

Description

Cacalone belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Cacalon is found in Cacalia decomposita, Ligularia cyathiceps and Ligularia virgaurea. Cacalon was first documented in 2006 (PMID: 16307855). Based on a literature review a small amount of articles have been published on Cacalone (PMID: 34068304) (PMID: 30572603) (PMID: 22908555) (PMID: 19501281).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    3.9528   -0.9962   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1979    0.0845   -0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8613    1.1304    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9525    1.9160    1.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7504    1.4721    0.8564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8539    0.3031    0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7078   -0.4699   -0.3604 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8482   -1.8858    0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7157   -0.5788   -1.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6098    0.1074   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7433    1.2226    0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0539    1.8048    1.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2344    1.2391    0.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9869    0.2622   -0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145   -0.6497   -0.4914 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2387   -1.7146    0.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4270    1.9880    1.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2952    3.0514    1.8364 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1350   -1.8748   -0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9585   -0.6481   -0.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4360   -1.2743   -1.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371    1.2697    0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7930   -1.9145    1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377   -2.5464   -0.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880   -2.3100   -0.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691    0.3430   -2.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9660    2.9191    0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1617    1.6780    2.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8266    2.0871   -0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9493    0.7775    1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8965    0.7859   -1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8899   -0.3835   -0.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6239   -1.1541   -1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2778   -1.5157    0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3434   -2.7249   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6004   -1.8006    1.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  2  0
 10  7  1  0
  7  8  1  0
  7  9  1  6
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  5 17  1  0
 17 18  2  0
 10 15  1  0
  2  6  1  0
 17 11  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 15 33  1  6
 14 31  1  0
 14 32  1  0
 13 29  1  0
 13 30  1  0
 12 27  1  0
 12 28  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  3 22  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652304282208342D          

 18 20  0  0  1  0            999 V2000
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2505    3.0764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0251    3.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  1  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 14 17  1  0  0  0  0
  3 18  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0061866

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCCC2=C1[C@@](C)(O)C1=C(OC=C1C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-8-5-4-6-10-11(8)15(3,17)12-9(2)7-18-14(12)13(10)16/h7-8,17H,4-6H2,1-3H3/t8-,15+/m0/s1

> <INCHI_KEY>
VNNQNPHIASWXBS-VXJOIVPMSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.306

> <EXACT_MASS>
246.12559444

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.029572868194908

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,5S)-4-hydroxy-3,4,5-trimethyl-4H,5H,6H,7H,8H,9H-naphtho[2,3-b]furan-9-one

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
2.409631537333333

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.107663816139222

> <JCHEM_PKA_STRONGEST_BASIC>
-2.941493052679379

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
69.4393

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,5S)-4-hydroxy-3,4,5-trimethyl-5H,6H,7H,8H-naphtho[2,3-b]furan-9-one

> <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       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.201   5.743   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.647   5.743   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10    4   12   13                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15    9                                                       
CONECT   17   14                                                            
CONECT   18    3                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₃

Average Mass

246.3060 Da

Monoisotopic Mass

246.12559 Da

IUPAC Name

(4R,5S)-4-hydroxy-3,4,5-trimethyl-4H,5H,6H,7H,8H,9H-naphtho[2,3-b]furan-9-one

Traditional Name

(4R,5S)-4-hydroxy-3,4,5-trimethyl-5H,6H,7H,8H-naphtho[2,3-b]furan-9-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CCCC2=C1[C@@](C)(O)C1=C(OC=C1C)C2=O

InChI Identifier

InChI=1S/C15H18O3/c1-8-5-4-6-10-11(8)15(3,17)12-9(2)7-18-14(12)13(10)16/h7-8,17H,4-6H2,1-3H3/t8-,15+/m0/s1

InChI Key

VNNQNPHIASWXBS-VXJOIVPMSA-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
Cacalia decomposita	Plant	KNApSAcK
Ligularia cyathiceps	LOTUS Database	35616633
Ligularia virgaurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Aryl ketone
Heteroaromatic compound
Tertiary alcohol
Furan
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.27	ALOGPS
logP	2.41	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.11	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.44 m³·mol⁻¹	ChemAxon
Polarizability	27.03 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00017504

Chemspider ID

558101

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

642921

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jimenez-Estrada M, Huerta-Reyes M, Tavera-Hernandez R, Alvarado-Sansininea JJ, Alvarez AB: Contributions from Mexican Flora for the Treatment of Diabetes Mellitus: Molecules of Psacalium decompositum (A. Gray) H. Rob & Brettell. Molecules. 2021 May 13;26(10). pii: molecules26102892. doi: 10.3390/molecules26102892. [PubMed:34068304 ]
Castillo-Arellano JI, Gomez-Verjan JC, Rojano-Vilchis NA, Mendoza-Cruz M, Jimenez-Estrada M, Lopez-Valdes HE, Martinez-Coria H, Gutierrez-Juarez R, Gonzalez-Espinosa C, Reyes-Chilpa R, Arrieta-Cruz I: Chemoinformatic Analysis of Selected Cacalolides from Psacalium decompositum (A. Gray) H. Rob. & Brettell and Psacalium peltatum (Kunth) Cass. and Their Effects on FcepsilonRI-Dependent Degranulation in Mast Cells. Molecules. 2018 Dec 19;23(12). pii: molecules23123367. doi: 10.3390/molecules23123367. [PubMed:30572603 ]
Garduno-Ramirez ML, Clares B, Dominguez-Villegas V, Peraire C, Ruiz MA, Garcia ML, Calpena AC: Skin permeation of cacalol, cacalone and 6-epi-cacalone sesquiterpenes from a nanoemulsion. Nat Prod Commun. 2012 Jul;7(7):821-3. [PubMed:22908555 ]
Campos MG, Oropeza M, Torres-Sosa C, Jimenez-Estrada M, Reyes-Chilpa R: Sesquiterpenoids from antidiabetic Psacalium decompositum block ATP sensitive potassium channels. J Ethnopharmacol. 2009 Jun 25;123(3):489-93. doi: 10.1016/j.jep.2009.03.003. Epub 2009 Mar 20. [PubMed:19501281 ]
Jimenez-Estrada M, Chilpa RR, Apan TR, Lledias F, Hansberg W, Arrieta D, Aguilar FJ: Anti-inflammatory activity of cacalol and cacalone sesquiterpenes isolated from Psacalium decompositum. J Ethnopharmacol. 2006 Apr 21;105(1-2):34-8. doi: 10.1016/j.jep.2005.09.039. Epub 2005 Nov 22. [PubMed:16307855 ]

Showing NP-Card for Cacalon (NP0061866)

MOL for NP0061866 (Cacalon)

3D MOL for NP0061866 (Cacalon)

3D SDF for NP0061866 (Cacalon)

3D-SDF for NP0061866 (Cacalon)

PDB for NP0061866 (Cacalon)

3D PDB for NP0061866 (Cacalon)

SMILES for NP0061866 (Cacalon)

INCHI for NP0061866 (Cacalon)

Structure for NP0061866 (Cacalon)

3D Structure for NP0061866 (Cacalon)