NP-MRD: Showing NP-Card for (3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one (NP0181758)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 20:20:03 UTC

Updated at

2022-09-03 20:20:03 UTC

NP-MRD ID

NP0181758

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one

Description

Costunolide belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. (3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one is found in Anthemis melampodina, Aristolochia yunnanensis, Artemisia genipi, Eria mucronata, Frullania lobulata, Magnolia virginiana and Staehelina fruticosa. (3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one was first documented in 2022 (PMID: 35723427). Based on a literature review a small amount of articles have been published on Costunolide (PMID: 35718516) (PMID: 35710877).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    3.6651    0.9241   -0.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7932    1.0168    0.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8028    2.0707    1.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6749    2.9685    1.4804 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6998    1.8604    2.2793 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7517    1.0553    1.5686 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1203    1.9043    0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450    1.5881    0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0849    2.5542   -0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532    0.3259    0.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3870   -0.3387   -0.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9186   -1.6973   -0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7976   -2.3067   -0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419   -3.7820   -0.9748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4263   -1.7758    0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482   -0.4730   -0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.1792    0.7225 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6111    0.1339   -1.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4800    1.6267   -0.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1996    0.4831    2.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3531    2.8606    0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1796    2.5109   -0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139    3.5879   -0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8842    2.4009   -1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918    0.6956    1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5390   -0.2534    1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5182   -0.2792   -0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0643    0.2546   -1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6901   -2.3380   -1.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3538   -4.3394   -0.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5445   -4.1443   -1.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1979   -3.8819   -1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2256   -1.7798    1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939   -2.5049   -0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7704   -0.6750   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559    0.1712   -0.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0283   -0.6036    1.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  7  2  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
  2 17  1  0
 17 16  1  0
 16 15  1  0
 15 13  1  0
 17  6  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 12 29  1  0
 11 27  1  0
 11 28  1  0
 10 25  1  0
 10 26  1  0
  9 22  1  0
  9 23  1  0
  9 24  1  0
  7 21  1  0
  6 20  1  1
  1 18  1  0
  1 19  1  0
 17 37  1  1
 16 35  1  0
 16 36  1  0
 15 33  1  0
 15 34  1  0
M  END


  Mrv1652309032222202D          

 17 18  0  0  1  0            999 V2000
    1.8304   -1.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460   -1.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -0.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614   -0.5125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2755   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124   -0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -0.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929   -1.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -1.2843    0.0000 C   0  0  1  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  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17  2  1  1  0  0  0
  6 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0181758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/CC\C(C)=C\[C@@H]2OC(=O)C(=C)[C@@H]2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5+,11-9+/t13-,14-/m0/s1

> <INCHI_KEY>
HRYLQFBHBWLLLL-NNHLIDDTSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.323

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
25.97511233663583

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,11aS)-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_LOGP>
3.8161666466666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.874751124392721

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
69.9464

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,11aS)-6,10-dimethyl-3-methylidene-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       3.417  -3.528   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.379  -2.326   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.972  -0.840   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.531  -0.296   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.259   0.006   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.461  -0.957   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.981  -0.707   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.525   0.734   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.549   1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.044   0.983   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.020  -0.208   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.476  -1.649   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.957  -1.898   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.467  -1.508   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.413  -3.339   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.893  -3.589   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.917  -2.397   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
Isocostunolide	MeSH

Chemical Formula

C₁₅H₂₀O₂

Average Mass

232.3230 Da

Monoisotopic Mass

232.14633 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C1=C/CC\C(C)=C\[C@@H]2OC(=O)C(=C)[C@@H]2CC1

InChI Identifier

InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/b10-5+,11-9+/t13-,14-/m0/s1

InChI Key

HRYLQFBHBWLLLL-NNHLIDDTSA-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
Anthemis melampodina	LOTUS Database	35616633
Aristolochia yunnanensis	LOTUS Database	35616633
Artemisia genipi	LOTUS Database	35616633
Eria mucronata	LOTUS Database	35616633
Frullania lobulata	LOTUS Database	35616633
Magnolia virginiana	LOTUS Database	35616633
Staehelina fruticosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Oxolane
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

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003240

Chemspider ID

78429572

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Costunolide

METLIN ID

Not Available

PubChem Compound

12304109

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shi Y, Dong T, Zeng B, Yao M, Wang Y, Xie Z, Xiao W, Yuan Y: Production of Plant Sesquiterpene Lactone Parthenolide in the Yeast Cell Factory. ACS Synth Biol. 2022 Jul 15;11(7):2473-2483. doi: 10.1021/acssynbio.2c00132. Epub 2022 Jun 20. [PubMed:35723427 ]
Ran QS, Mu J, Li T, Shen S, Xu J, Li X, Gu WW, DU MB, Liu SZ: [Research of preparation quality markers of Yulian Tang with anti-inflammatory activity]. Zhongguo Zhong Yao Za Zhi. 2022 Jun;47(11):2947-2954. doi: 10.19540/j.cnki.cjcmm.20220118.301. [PubMed:35718516 ]
Huang ZQ, Luo W, Li WX, Chen P, Wang Z, Chen RJ, Wang Y, Huang WJ, Liang G: Costunolide alleviates atherosclerosis in high-fat diet-fed ApoE(-/-) mice through covalently binding to IKKbeta and inhibiting NF-kappaB-mediated inflammation. Acta Pharmacol Sin. 2023 Jan;44(1):58-70. doi: 10.1038/s41401-022-00928-0. Epub 2022 Jun 16. [PubMed:35710877 ]
LOTUS database [Link]

Showing NP-Card for (3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one (NP0181758)

MOL for NP0181758 ((3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

3D MOL for NP0181758 ((3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

3D SDF for NP0181758 ((3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

3D-SDF for NP0181758 ((3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

PDB for NP0181758 ((3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

3D PDB for NP0181758 ((3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

SMILES for NP0181758 ((3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

INCHI for NP0181758 ((3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

Structure for NP0181758 ((3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)

3D Structure for NP0181758 ((3as,11as)-6,10-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one)