NP-MRD: Showing NP-Card for Isodehydrocostus lactone (NP0063816)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 08:09:36 UTC

Updated at

2022-04-28 08:09:36 UTC

NP-MRD ID

NP0063816

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isodehydrocostus lactone

Description

Isodehydrocostus lactone belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Isodehydrocostus lactone is found in Saussurea lappa . Based on a literature review very few articles have been published on Isodehydrocostus lactone.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    1.7709    2.5619   -2.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5436    1.4048   -1.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5536    0.3249   -1.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6051    0.3227   -2.4004 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0778   -0.5741   -0.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9213   -0.0746   -0.1241 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3465    0.8604   -1.1210 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4021    2.0130   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870    1.6159   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9775    0.1395   -0.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -0.2379   -1.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3451   -0.9551    0.5895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2375   -0.5072    2.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1799   -1.4647    2.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590   -1.8691    1.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -2.8110    1.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0803   -1.2282    0.2846 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7350    2.7969   -2.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0389    3.3509   -2.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2682    0.4899    0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2723    0.3064   -1.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4705    2.8245   -1.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2079    2.3998    0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223    2.1321   -0.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9343    2.0074    0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3876    0.4822   -1.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0507   -1.2858   -1.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -1.8648    0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996    0.5309    2.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1817   -0.7114    2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0907   -1.7403    3.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1384   -2.9996    0.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5231   -2.4104    2.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4200   -3.7831    2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0934   -2.0473   -0.4863 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 17  1  0
 17  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 17 15  1  0
  7  6  1  0
 10 12  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 14 31  1  0
 13 29  1  0
 13 30  1  0
 12 28  1  1
 17 35  1  6
  6 20  1  1
  1 18  1  0
  1 19  1  0
  7 21  1  6
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
M  END


  Mrv1652304282210092D          

 17 19  0  0  1  0            999 V2000
    4.9157    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1803   -0.8820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9527   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412   -1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534   -2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651   -2.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265   -0.8820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8409   -0.2370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3864    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  6  0  0  0
 14 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063816

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC[C@@H]2[C@H]1[C@H]1OC(=O)C(=C)[C@@H]1CCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h5,11-14H,1,3-4,6-7H2,2H3/t11-,12-,13-,14-/m0/s1

> <INCHI_KEY>
HOKNRQOXIXGZDY-XUXIUFHCSA-N

> <FORMULA>
C15H18O2

> <MOLECULAR_WEIGHT>
230.307

> <EXACT_MASS>
230.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.891604714023636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,6aR,9aR,9bS)-9-methyl-3,6-dimethylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.017321547

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.865903943172365

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
67.0439

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,6aR,9aR,9bS)-9-methyl-3,6-dimethylidene-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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       9.176   0.433   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.380   1.393   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.691   0.843   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.843  -0.442   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.803  -1.646   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.245  -1.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.530  -1.954   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.461  -3.148   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.073  -3.816   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.686  -3.148   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.482  -4.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.343  -1.646   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.303  -0.442   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.455   0.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.970   0.433   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.901  -1.105   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.996   2.285   0.000  0.00  0.00           C+0
CONECT    1    2    3    6                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12    4   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₂

Average Mass

230.3070 Da

Monoisotopic Mass

230.13068 Da

IUPAC Name

(3aS,6aR,9aR,9bS)-9-methyl-3,6-dimethylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

Traditional Name

(3aS,6aR,9aR,9bS)-9-methyl-3,6-dimethylidene-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC1=CC[C@@H]2[C@H]1[C@H]1OC(=O)C(=C)[C@@H]1CCC2=C

InChI Identifier

InChI=1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h5,11-14H,1,3-4,6-7H2,2H3/t11-,12-,13-,14-/m0/s1

InChI Key

HOKNRQOXIXGZDY-XUXIUFHCSA-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
Saussurea costus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
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

sesquiterpene lactone (CHEBI:81376 )

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	3.41	ALOGPS
logP	3.02	ChemAxon
logS	-3	ALOGPS
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	67.04 m³·mol⁻¹	ChemAxon
Polarizability	25.89 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

C00020714

Chemspider ID

9108528

KEGG Compound ID

C17913

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10933292

PDB ID

Not Available

ChEBI ID

81376

Good Scents ID

Not Available

References

General References

Showing NP-Card for Isodehydrocostus lactone (NP0063816)

MOL for NP0063816 (Isodehydrocostus lactone)

3D MOL for NP0063816 (Isodehydrocostus lactone)

3D SDF for NP0063816 (Isodehydrocostus lactone)

3D-SDF for NP0063816 (Isodehydrocostus lactone)

PDB for NP0063816 (Isodehydrocostus lactone)

3D PDB for NP0063816 (Isodehydrocostus lactone)

SMILES for NP0063816 (Isodehydrocostus lactone)

INCHI for NP0063816 (Isodehydrocostus lactone)

Structure for NP0063816 (Isodehydrocostus lactone)

3D Structure for NP0063816 (Isodehydrocostus lactone)