NP-MRD: Showing NP-Card for 8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate (NP0329591)

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Record Information

Version

2.0

Created at

2022-09-12 14:07:11 UTC

Updated at

2022-09-12 14:07:11 UTC

NP-MRD ID

NP0329591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate

Description

8A-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate 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. 8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate is found in Farfugium japonicum. Based on a literature review very few articles have been published on 8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122216072D          

 31 33  0  0  0  0            999 V2000
   -2.1434   -2.8875    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  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
    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  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    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
    2.8579    0.8250    0.0000 O   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 O   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
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    4.2868    3.3000    0.0000 C   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
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M  END

     RDKit          3D

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M  END


  Mrv1652309122216072D          

 31 33  0  0  0  0            999 V2000
   -2.1434   -2.8875    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
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M  END
> <DATABASE_ID>
NP0329591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC1CCC2(O)C(OC(=O)C=C(C)C)C3=C(CC2(C)C1C)C(C)=CO3

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O6/c1-8-15(4)23(27)30-19-9-10-25(28)22(31-20(26)11-14(2)3)21-18(16(5)13-29-21)12-24(25,7)17(19)6/h8,11,13,17,19,22,28H,9-10,12H2,1-7H3

> <INCHI_KEY>
QCTUXXJYMYWQOB-UHFFFAOYSA-N

> <FORMULA>
C25H34O6

> <MOLECULAR_WEIGHT>
430.541

> <EXACT_MASS>
430.235538815

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
47.76310736839131

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate

> <JCHEM_LOGP>
5.472308434333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.16564394358031

> <JCHEM_PKA_STRONGEST_BASIC>
-2.754404698626538

> <JCHEM_POLAR_SURFACE_AREA>
85.97000000000001

> <JCHEM_REFRACTIVITY>
118.40559999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4H,5H,6H,7H,8H,9H-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

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      -4.001  -5.390   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  O   UNK     0       4.001   0.770   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  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.609  -4.251   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -3.080   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
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   30                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   28                                             
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   13   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   21   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   11   29   30                                             
CONECT   29   28                                                            
CONECT   30   28    8   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
8a-Hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₄O₆

Average Mass

430.5410 Da

Monoisotopic Mass

430.23554 Da

IUPAC Name

8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate

Traditional Name

8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4H,5H,6H,7H,8H,9H-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1CCC2(O)C(OC(=O)C=C(C)C)C3=C(CC2(C)C1C)C(C)=CO3

InChI Identifier

InChI=1S/C25H34O6/c1-8-15(4)23(27)30-19-9-10-25(28)22(31-20(26)11-14(2)3)21-18(16(5)13-29-21)12-24(25,7)17(19)6/h8,11,13,17,19,22,28H,9-10,12H2,1-7H3

InChI Key

QCTUXXJYMYWQOB-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
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
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Furan
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen 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	5.47	ChemAxon
pKa (Strongest Acidic)	13.17	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.97 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	118.41 m³·mol⁻¹	ChemAxon
Polarizability	47.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

162990019

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate (NP0329591)

MOL for NP0329591 (8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate)

3D MOL for NP0329591 (8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate)

3D SDF for NP0329591 (8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate)

3D-SDF for NP0329591 (8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate)

PDB for NP0329591 (8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate)

3D PDB for NP0329591 (8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate)

SMILES for NP0329591 (8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate)

INCHI for NP0329591 (8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate)

Structure for NP0329591 (8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate)

3D Structure for NP0329591 (8a-hydroxy-3,4a,5-trimethyl-6-[(2-methylbut-2-enoyl)oxy]-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-9-yl 3-methylbut-2-enoate)