NP-MRD: Showing NP-Card for (4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate (NP0325880)

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Record Information

Version

2.0

Created at

2022-09-12 06:58:53 UTC

Updated at

2022-09-12 06:58:54 UTC

NP-MRD ID

NP0325880

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate

Description

3Beta-Angeloyloxyfuranoeremophilane 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. (4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate is found in Farfugium japonicum. Based on a literature review very few articles have been published on 3beta-Angeloyloxyfuranoeremophilane.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122208582D          

 23 25  0  0  1  0            999 V2000
   -1.4289   -1.6500    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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   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   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  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
    1.4289    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  2  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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -2.2771    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  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
    1.4289   -1.6500    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 13 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0325880

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@H]1CC[C@@H]2CC3=C(C[C@]2(C)[C@H]1C)C(C)=CO3

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-6-12(2)19(21)23-17-8-7-15-9-18-16(13(3)11-22-18)10-20(15,5)14(17)4/h6,11,14-15,17H,7-10H2,1-5H3/b12-6-/t14-,15+,17-,20+/m0/s1

> <INCHI_KEY>
JXWIRRRZGAWCPK-JJLSJPPXSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.52160387125138

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,5R,6S,8aR)-3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-6-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
5.333948869333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6394869646810437

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
92.0693

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,5R,6S,8aR)-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-6-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   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  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.609  -4.251   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -4.620   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   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   11   21   22                                             
CONECT   21   20                                                            
CONECT   22   20    8   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
3b-Angeloyloxyfuranoeremophilane	Generator
3Β-angeloyloxyfuranoeremophilane	Generator

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4410 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

(4aS,5R,6S,8aR)-3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-6-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(4aS,5R,6S,8aR)-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-6-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@H]1CC[C@@H]2CC3=C(C[C@]2(C)[C@H]1C)C(C)=CO3

InChI Identifier

InChI=1S/C20H28O3/c1-6-12(2)19(21)23-17-8-7-15-9-18-16(13(3)11-22-18)10-20(15,5)14(17)4/h6,11,14-15,17H,7-10H2,1-5H3/b12-6-/t14-,15+,17-,20+/m0/s1

InChI Key

JXWIRRRZGAWCPK-JJLSJPPXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Farfugium japonicum	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
Fatty acid ester
Fatty acyl
Furan
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	5.33	ChemAxon
pKa (Strongest Basic)	-2.6	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	92.07 m³·mol⁻¹	ChemAxon
Polarizability	36.52 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

C00017367

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

101596873

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate (NP0325880)

MOL for NP0325880 ((4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0325880 ((4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0325880 ((4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0325880 ((4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate)

PDB for NP0325880 ((4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0325880 ((4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0325880 ((4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0325880 ((4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate)

Structure for NP0325880 ((4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0325880 ((4as,5r,6s,8ar)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-6-yl (2z)-2-methylbut-2-enoate)