NP-MRD: Showing NP-Card for 4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate (NP0301622)

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Record Information

Version

2.0

Created at

2022-09-10 14:42:14 UTC

Updated at

2022-09-10 14:42:15 UTC

NP-MRD ID

NP0301622

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate

Description

4-[(Acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5H,6H,7H,8H-naphtho[2,3-b]furan-7-yl 3-methylbutanoate 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. 4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate is found in Senecio lydenburgensis. 4-[(Acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5H,6H,7H,8H-naphtho[2,3-b]furan-7-yl 3-methylbutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241505372D          

 32 34  0  0  0  0            999 V2000
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7859    0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0409    0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2708    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7859    2.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
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  3  5  1  0  0  0  0
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M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
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   -1.2779   -2.0228    2.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9594   -1.4052    1.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004241505372D          

 32 34  0  0  0  0            999 V2000
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0409    0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0301622

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)OC1=C2OC=C(C)C2=C(COC(C)=O)C2=C1CC(CC2C)OC(=O)CC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O7/c1-7-20(27)32-24-18-10-17(31-21(28)8-13(2)3)9-14(4)22(18)19(12-29-16(6)26)23-15(5)11-30-25(23)24/h11,13-14,17H,7-10,12H2,1-6H3

> <INCHI_KEY>
KRJWCHKBOZVTOO-UHFFFAOYSA-N

> <FORMULA>
C25H32O7

> <MOLECULAR_WEIGHT>
444.524

> <EXACT_MASS>
444.21480337

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.374831569007796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5H,6H,7H,8H-naphtho[2,3-b]furan-7-yl 3-methylbutanoate

> <ALOGPS_LOGP>
4.56

> <JCHEM_LOGP>
4.853166864333334

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8757439928323594

> <JCHEM_POLAR_SURFACE_AREA>
92.04000000000002

> <JCHEM_REFRACTIVITY>
118.29529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5H,6H,7H,8H-naphtho[2,3-b]furan-7-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0     -10.669   6.160   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -8.002   6.160   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -10.800   1.834   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -11.276   0.369   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -11.706   3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -10.800   4.326   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334   2.310   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                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14   21   25                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    6   20                                                  
CONECT   26    9   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
4-[(Acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5H,6H,7H,8H-naphtho[2,3-b]furan-7-yl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₅H₃₂O₇

Average Mass

444.5240 Da

Monoisotopic Mass

444.21480 Da

IUPAC Name

4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5H,6H,7H,8H-naphtho[2,3-b]furan-7-yl 3-methylbutanoate

Traditional Name

4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5H,6H,7H,8H-naphtho[2,3-b]furan-7-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CCC(=O)OC1=C2OC=C(C)C2=C(COC(C)=O)C2=C1CC(CC2C)OC(=O)CC(C)C

InChI Identifier

InChI=1S/C25H32O7/c1-7-20(27)32-24-18-10-17(31-21(28)8-13(2)3)9-14(4)22(18)19(12-29-16(6)26)23-15(5)11-30-25(23)24/h11,13-14,17H,7-10,12H2,1-6H3

InChI Key

KRJWCHKBOZVTOO-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
Senecio lydenburgensis	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
Tetralin
Benzofuran
Tricarboxylic acid or derivatives
Fatty acid ester
Benzenoid
Fatty acyl
Heteroaromatic compound
Furan
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
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	4.56	ALOGPS
logP	4.85	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	92.04 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	118.3 m³·mol⁻¹	ChemAxon
Polarizability	49.37 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	Yes	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 4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate (NP0301622)

MOL for NP0301622 (4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate)

3D MOL for NP0301622 (4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate)

3D SDF for NP0301622 (4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate)

3D-SDF for NP0301622 (4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate)

PDB for NP0301622 (4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate)

3D PDB for NP0301622 (4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate)

SMILES for NP0301622 (4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate)

INCHI for NP0301622 (4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate)

Structure for NP0301622 (4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate)

3D Structure for NP0301622 (4-[(acetyloxy)methyl]-3,5-dimethyl-9-(propanoyloxy)-5h,6h,7h,8h-naphtho[2,3-b]furan-7-yl 3-methylbutanoate)