NP-MRD: Showing NP-Card for α-cyclocostunolide (NP0185756)

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Record Information

Version

1.0

Created at

2022-09-04 01:17:48 UTC

Updated at

2022-09-04 01:17:48 UTC

NP-MRD ID

NP0185756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

α-cyclocostunolide

Description

Alpha-Cyclocostunolide belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. α-cyclocostunolide is found in Aristolochia griffithii, Critonia morifolia, Eremanthus erythropappus, Critonia quadrangularis, Frullania tamarisci, Loxothysanus sinuatus, Magnolia kachirachirai, Magnolia sinica, Oxylobus adscendens and Oxylobus oaxacanus. It was first documented in 2006 (PMID: 16864436). Based on a literature review a small amount of articles have been published on alpha-Cyclocostunolide (PMID: 25068579) (PMID: 21624443) (PMID: 26695888).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    4.1493    0.7121   -1.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1396    0.5352   -0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979    1.0826    1.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8818    1.7561    1.7892 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182    0.7266    1.6562 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9398    0.5445    0.5177 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9122   -0.2490   -0.3748 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3431   -0.1970   -1.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0820   -1.0713   -1.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759   -0.5968   -0.6662 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6028    0.6278   -1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9220   -1.6780   -0.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8201   -1.4441    0.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5253   -0.2500    1.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3275    0.3256    1.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1412    1.5218    2.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700   -0.2973    0.6746 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0149    1.3128   -0.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1639    0.2623   -1.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7641    1.5030   -0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9928   -1.2912   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9800    0.8359   -1.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0161   -0.5652   -2.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4440   -2.1082   -1.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176   -1.0437   -2.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631    1.5211   -0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6526    0.6062   -0.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    0.5774   -2.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4367   -2.6864   -0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005   -1.7506   -1.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -1.3844    0.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267   -2.3196    1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3268    0.1833    2.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1729    2.0278    2.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9376    2.2905    2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798    1.2307    3.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0214   -1.2506    1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  1  6
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  6 17  1  0
 17 15  1  0
 17 10  1  0
  2  7  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 14 33  1  0
 13 31  1  0
 13 32  1  0
 12 29  1  0
 12 30  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
  9 24  1  0
  9 25  1  0
  8 22  1  0
  8 23  1  0
  7 21  1  1
  6 20  1  6
  1 18  1  0
  1 19  1  0
 17 37  1  1
M  END


  Mrv1652309042203172D          

 17 19  0  0  1  0            999 V2000
    4.2295   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.4640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7983   -0.2372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4083   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.2887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7591   -1.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.4383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 15  1  6  0  0  0
  6 17  1  0  0  0  0
 10 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185756

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC[C@]2(C)CC[C@@H]3[C@H](OC(=O)C3=C)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-9-5-4-7-15(3)8-6-11-10(2)14(16)17-13(11)12(9)15/h5,11-13H,2,4,6-8H2,1,3H3/t11-,12+,13-,15+/m0/s1

> <INCHI_KEY>
UHODXTMZSDNATP-SFDCQRBFSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.323

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.463044102361245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,5aR,9aR,9bS)-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,9aH,9bH-naphtho[1,2-b]furan-2-one

> <JCHEM_LOGP>
3.377995381666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.8658774946809205

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
67.1929

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
α-cyclocostunolide

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       7.895  -1.070   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.719  -0.076   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.832   1.460   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.141   2.271   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.406   2.042   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.412   0.866   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.223  -0.443   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.495  -1.800   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.956  -1.848   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.145  -0.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.417  -1.896   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.606  -0.587   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.206   0.722   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.522   2.079   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.062   2.127   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.790   3.484   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.873   0.818   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   17                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    6   10                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
a-Cyclocostunolide	Generator
Α-cyclocostunolide	Generator
Cyclocostunolide	MeSH

Chemical Formula

C₁₅H₂₀O₂

Average Mass

232.3230 Da

Monoisotopic Mass

232.14633 Da

IUPAC Name

(3aS,5aR,9aR,9bS)-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,9aH,9bH-naphtho[1,2-b]furan-2-one

Traditional Name

α-cyclocostunolide

CAS Registry Number

Not Available

SMILES

CC1=CCC[C@]2(C)CC[C@@H]3[C@H](OC(=O)C3=C)[C@@H]12

InChI Identifier

InChI=1S/C15H20O2/c1-9-5-4-7-15(3)8-6-11-10(2)14(16)17-13(11)12(9)15/h5,11-13H,2,4,6-8H2,1,3H3/t11-,12+,13-,15+/m0/s1

InChI Key

UHODXTMZSDNATP-SFDCQRBFSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Aristolochia griffithii	LOTUS Database	35616633
Critonia morifolia	LOTUS Database	35616633
Eremanthus erythropappus	LOTUS Database	35616633
Eupatorium quadrangulare	LOTUS Database	35616633
Frullania tamarisci	LOTUS Database	35616633
Loxothysanus sinuatus	LOTUS Database	35616633
Magnolia kachirachirai	LOTUS Database	35616633
Manglietiastrum sinicum	LOTUS Database	35616633
Oxylobus adscendens	LOTUS Database	35616633
Oxylobus oaxacanus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:10226 )
Eudesmanes (C09383 )

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	3.38	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.19 m³·mol⁻¹	ChemAxon
Polarizability	26.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00003241

Chemspider ID

390699

KEGG Compound ID

C09383

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442191

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1043791

References

General References

Li S, An TY, Li J, Shen Q, Lou FC, Hu LH: PTP1B inhibitors from Saussrurea lappa. J Asian Nat Prod Res. 2006 Apr-May;8(3):281-6. doi: 10.1080/10286020412331286434. [PubMed:16864436 ]
Kumar A, Kumar S, Kumar D, Agnihotri VK: UPLC/MS/MS method for quantification and cytotoxic activity of sesquiterpene lactones isolated from Saussurea lappa. J Ethnopharmacol. 2014 Sep 11;155(2):1393-7. doi: 10.1016/j.jep.2014.07.037. Epub 2014 Jul 25. [PubMed:25068579 ]
Julianti T, Hata Y, Zimmermann S, Kaiser M, Hamburger M, Adams M: Antitrypanosomal sesquiterpene lactones from Saussurea costus. Fitoterapia. 2011 Oct;82(7):955-9. doi: 10.1016/j.fitote.2011.05.010. Epub 2011 May 23. [PubMed:21624443 ]
Lloyd MG, D'Acunto M, Taylor RJ, Unsworth WP: A selective C-H insertion/olefination protocol for the synthesis of alpha-methylene-gamma-butyrolactone natural products. Org Biomol Chem. 2016 Feb 7;14(5):1641-5. doi: 10.1039/c5ob02579f. [PubMed:26695888 ]
LOTUS database [Link]

Showing NP-Card for α-cyclocostunolide (NP0185756)

MOL for NP0185756 (α-cyclocostunolide)

3D MOL for NP0185756 (α-cyclocostunolide)

3D SDF for NP0185756 (α-cyclocostunolide)

3D-SDF for NP0185756 (α-cyclocostunolide)

PDB for NP0185756 (α-cyclocostunolide)

3D PDB for NP0185756 (α-cyclocostunolide)

SMILES for NP0185756 (α-cyclocostunolide)

INCHI for NP0185756 (α-cyclocostunolide)

Structure for NP0185756 (α-cyclocostunolide)

3D Structure for NP0185756 (α-cyclocostunolide)