NP-MRD: Showing NP-Card for 3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate (NP0285821)

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Record Information

Version

2.0

Created at

2022-09-09 14:09:24 UTC

Updated at

2022-09-09 14:09:24 UTC

NP-MRD ID

NP0285821

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate

Description

3,4A,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl 2-methylpropanoate 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. 3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate is found in Ligularia lamarum. 3,4A,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl 2-methylpropanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171522422D          

 22 24  0  0  0  0            999 V2000
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    3.6425    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  7 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)OC1C2=C(CC3CCCC(C)C13C)OC=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O3/c1-11(2)18(20)22-17-16-12(3)10-21-15(16)9-14-8-6-7-13(4)19(14,17)5/h10-11,13-14,17H,6-9H2,1-5H3

> <INCHI_KEY>
JRLAQPPIOLHSLM-UHFFFAOYSA-N

> <FORMULA>
C19H28O3

> <MOLECULAR_WEIGHT>
304.43

> <EXACT_MASS>
304.203844762

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
34.894577506918154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl 2-methylpropanoate

> <ALOGPS_LOGP>
5.15

> <JCHEM_LOGP>
5.0395203603333325

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.726863608711013

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
86.36139999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.53e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.799   2.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.275   3.481   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.705   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.799  -0.476   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    7   15   22                                             
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
3,4a,5-Trimethyl-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-4-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₁₉H₂₈O₃

Average Mass

304.4300 Da

Monoisotopic Mass

304.20384 Da

IUPAC Name

3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl 2-methylpropanoate

Traditional Name

3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)OC1C2=C(CC3CCCC(C)C13C)OC=C2C

InChI Identifier

InChI=1S/C19H28O3/c1-11(2)18(20)22-17-16-12(3)10-21-15(16)9-14-8-6-7-13(4)19(14,17)5/h10-11,13-14,17H,6-9H2,1-5H3

InChI Key

JRLAQPPIOLHSLM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ligularia lamarum	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
Benzofuran
Furan
Heteroaromatic compound
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
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	5.15	ALOGPS
logP	5.04	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.36 m³·mol⁻¹	ChemAxon
Polarizability	34.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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 3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate (NP0285821)

MOL for NP0285821 (3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate)

3D MOL for NP0285821 (3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate)

3D SDF for NP0285821 (3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate)

3D-SDF for NP0285821 (3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate)

PDB for NP0285821 (3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate)

3D PDB for NP0285821 (3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate)

SMILES for NP0285821 (3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate)

INCHI for NP0285821 (3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate)

Structure for NP0285821 (3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate)

3D Structure for NP0285821 (3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate)