NP-MRD: Showing NP-Card for 6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate (NP0248745)

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Record Information

Version

2.0

Created at

2022-09-07 11:06:41 UTC

Updated at

2022-09-07 11:06:41 UTC

NP-MRD ID

NP0248745

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate

Description

6,9-Dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-dodecahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate 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. 6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate is found in Calea ternifolia. 6,9-Dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-dodecahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151517552D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004151517552D          

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M  END
> <DATABASE_ID>
NP0248745

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)OC1C(OC(=O)C(C)=CC)C2C(CC(C)C(O)CC(=O)C1(C)O)OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O9/c1-8-12(3)22(28)33-20-19-15(6)24(30)32-17(19)10-14(5)16(26)11-18(27)25(7,31)21(20)34-23(29)13(4)9-2/h8,13-14,16-17,19-21,26,31H,6,9-11H2,1-5,7H3

> <INCHI_KEY>
QOEQYOLWGFTWNJ-UHFFFAOYSA-N

> <FORMULA>
C25H36O9

> <MOLECULAR_WEIGHT>
480.554

> <EXACT_MASS>
480.235932739

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.231959817089155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-dodecahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
3.6479269043333336

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.485959213178432

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.212648823410518

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9000547619910204

> <JCHEM_POLAR_SURFACE_AREA>
136.43

> <JCHEM_REFRACTIVITY>
121.54509999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.239  -1.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.040  -1.494   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.295  -1.494   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.013   3.816   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.518   3.977   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.288   5.311   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.144   2.570   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.651   2.250   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17    9   18   33                                                  
CONECT   18   17   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    8   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   18   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   17   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Value	Source
6,9-Dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-dodecahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₆O₉

Average Mass

480.5540 Da

Monoisotopic Mass

480.23593 Da

IUPAC Name

6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-dodecahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate

Traditional Name

6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)OC1C(OC(=O)C(C)=CC)C2C(CC(C)C(O)CC(=O)C1(C)O)OC(=O)C2=C

InChI Identifier

InChI=1S/C25H36O9/c1-8-12(3)22(28)33-20-19-15(6)24(30)32-17(19)10-14(5)16(26)11-18(27)25(7,31)21(20)34-23(29)13(4)9-2/h8,13-14,16-17,19-21,26,31H,6,9-11H2,1-5,7H3

InChI Key

QOEQYOLWGFTWNJ-UHFFFAOYSA-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
Calea ternifolia	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
Tricarboxylic acid or derivatives
Fatty acid ester
Acyloin
Cyclitol or derivatives
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
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	1.7	ALOGPS
logP	3.65	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	136.43 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.55 m³·mol⁻¹	ChemAxon
Polarizability	50.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate (NP0248745)

MOL for NP0248745 (6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate)

3D MOL for NP0248745 (6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate)

3D SDF for NP0248745 (6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate)

3D-SDF for NP0248745 (6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate)

PDB for NP0248745 (6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate)

3D PDB for NP0248745 (6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate)

SMILES for NP0248745 (6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate)

INCHI for NP0248745 (6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate)

Structure for NP0248745 (6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate)

3D Structure for NP0248745 (6,9-dihydroxy-6,10-dimethyl-5-[(2-methylbutanoyl)oxy]-3-methylidene-2,7-dioxo-octahydrocyclodeca[b]furan-4-yl 2-methylbut-2-enoate)