NP-MRD: Showing NP-Card for 7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate (NP0253050)

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Record Information

Version

2.0

Created at

2022-09-07 16:48:08 UTC

Updated at

2022-09-07 16:48:08 UTC

NP-MRD ID

NP0253050

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate

Description

7-(Acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1H,3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-4-yl acetate belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. 7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate is found in Cunninghamia lanceolata. 7-(Acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1H,3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241502162D          

 35 38  0  0  0  0            999 V2000
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    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
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M  END

     RDKit          3D

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M  END


  Mrv1533004241502162D          

 35 38  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0253050

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1OC(C)=O)C1C2COCC2C(OC(C)=O)C2=CC(OC)=C(OC(C)=O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O9/c1-13(27)33-21-7-6-16(8-22(21)30-4)25-17-9-24(34-14(2)28)23(31-5)10-18(17)26(35-15(3)29)20-12-32-11-19(20)25/h6-10,19-20,25-26H,11-12H2,1-5H3

> <INCHI_KEY>
VJERPUFNZZFMSD-UHFFFAOYSA-N

> <FORMULA>
C26H28O9

> <MOLECULAR_WEIGHT>
484.501

> <EXACT_MASS>
484.173332482

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
50.07086320048792

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1H,3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-4-yl acetate

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
2.0156655703333346

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.00091499715077

> <JCHEM_POLAR_SURFACE_AREA>
106.59

> <JCHEM_REFRACTIVITY>
123.23370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.99e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1H,3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-4-yl acetate

> <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       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335   6.160   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  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.799   2.016   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.705   0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.799  -0.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    5   14   35                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   35                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   35                                                       
CONECT   35   34   13   24                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
7-(Acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1H,3H,3ah,4H,9H,9ah-naphtho[2,3-c]furan-4-yl acetic acid	Generator

Chemical Formula

C₂₆H₂₈O₉

Average Mass

484.5010 Da

Monoisotopic Mass

484.17333 Da

IUPAC Name

7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1H,3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-4-yl acetate

Traditional Name

7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1H,3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-4-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1OC(C)=O)C1C2COCC2C(OC(C)=O)C2=CC(OC)=C(OC(C)=O)C=C12

InChI Identifier

InChI=1S/C26H28O9/c1-13(27)33-21-7-6-16(8-22(21)30-4)25-17-9-24(34-14(2)28)23(31-5)10-18(17)26(35-15(3)29)20-12-32-11-19(20)25/h6-10,19-20,25-26H,11-12H2,1-5H3

InChI Key

VJERPUFNZZFMSD-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
Cunninghamia lanceolata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

Not Available

Direct Parent

Aryltetralin lignans

Alternative Parents

Substituents

1-aryltetralin lignan
Naphthofuran
Phenol ester
Tetralin
Tricarboxylic acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	3.58	ALOGPS
logP	2.02	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	106.59 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	123.23 m³·mol⁻¹	ChemAxon
Polarizability	50.07 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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 7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate (NP0253050)

MOL for NP0253050 (7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate)

3D MOL for NP0253050 (7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate)

3D SDF for NP0253050 (7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate)

3D-SDF for NP0253050 (7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate)

PDB for NP0253050 (7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate)

3D PDB for NP0253050 (7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate)

SMILES for NP0253050 (7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate)

INCHI for NP0253050 (7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate)

Structure for NP0253050 (7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate)

3D Structure for NP0253050 (7-(acetyloxy)-9-[4-(acetyloxy)-3-methoxyphenyl]-6-methoxy-1h,3h,3ah,4h,9h,9ah-naphtho[2,3-c]furan-4-yl acetate)