NP-MRD: Showing NP-Card for [5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate (NP0193163)

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Record Information

Version

2.0

Created at

2022-09-04 10:32:20 UTC

Updated at

2022-09-04 10:32:21 UTC

NP-MRD ID

NP0193163

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate

Description

[8-(Acetyloxy)-9-hydroxy-16-methoxy-2,6,11-trimethyl-14-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]Heptadec-12-en-6-yl]methyl acetate belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. [5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate is found in Myrospermum frutescens. [8-(Acetyloxy)-9-hydroxy-16-methoxy-2,6,11-trimethyl-14-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]Heptadec-12-en-6-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151517562D          

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M  END

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M  END


  Mrv1533004151517562D          

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M  END
> <DATABASE_ID>
NP0193163

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC12CC3C(C(O)C(OC(C)=O)C4C(C)(COC(C)=O)CCCC34C)C(C)C1=CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O8/c1-13-16-10-18(28)33-25(16,30-6)11-17-19(13)20(29)21(32-15(3)27)22-23(4,12-31-14(2)26)8-7-9-24(17,22)5/h10,13,17,19-22,29H,7-9,11-12H2,1-6H3

> <INCHI_KEY>
HDDNZVWBRRAOGK-UHFFFAOYSA-N

> <FORMULA>
C25H36O8

> <MOLECULAR_WEIGHT>
464.555

> <EXACT_MASS>
464.241018119

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.64420392482249

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[8-(acetyloxy)-9-hydroxy-16-methoxy-2,6,11-trimethyl-14-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadec-12-en-6-yl]methyl acetate

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
2.393454701

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.293021897295986

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.790382272676514

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2835472619869766

> <JCHEM_POLAR_SURFACE_AREA>
108.36

> <JCHEM_REFRACTIVITY>
117.59599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[8-(acetyloxy)-9-hydroxy-16-methoxy-2,6,11-trimethyl-14-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadec-12-en-6-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       8.245  -4.466   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.356  -3.399   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.987  -1.904   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.503  -2.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.495  -0.998   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.972   0.451   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.965   1.628   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.442   3.076   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.481   1.357   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.473   2.534   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.950   3.982   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.434   4.254   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.943   5.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.004  -0.092   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.520  -0.363   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.524   1.177   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.037  -0.099   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.567   1.347   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      19.085   1.611   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      19.615   3.057   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      20.072   0.429   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.043  -1.811   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.050  -2.988   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.534  -2.717   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.011  -1.269   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.019  -2.446   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.456   0.722   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.933   2.170   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.463  -0.456   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.924  -0.506   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.496  -1.985   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.048  -2.508   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       7.771  -2.849   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29   33                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   25                                                  
CONECT   15   14   16   17   22                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    5   14   26                                             
CONECT   26   25                                                            
CONECT   27    6   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    3   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
[8-(Acetyloxy)-9-hydroxy-16-methoxy-2,6,11-trimethyl-14-oxo-15-oxatetracyclo[8.7.0.0,.0,]heptadec-12-en-6-yl]methyl acetic acid	Generator
[8-(Acetyloxy)-9-hydroxy-16-methoxy-2,6,11-trimethyl-14-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadec-12-en-6-yl]methyl acetic acid	Generator

Chemical Formula

C₂₅H₃₆O₈

Average Mass

464.5550 Da

Monoisotopic Mass

464.24102 Da

IUPAC Name

[8-(acetyloxy)-9-hydroxy-16-methoxy-2,6,11-trimethyl-14-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadec-12-en-6-yl]methyl acetate

Traditional Name

[8-(acetyloxy)-9-hydroxy-16-methoxy-2,6,11-trimethyl-14-oxo-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadec-12-en-6-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

COC12CC3C(C(O)C(OC(C)=O)C4C(C)(COC(C)=O)CCCC34C)C(C)C1=CC(=O)O2

InChI Identifier

InChI=1S/C25H36O8/c1-13-16-10-18(28)33-25(16,30-6)11-17-19(13)20(29)21(32-15(3)27)22-23(4,12-31-14(2)26)8-7-9-24(17,22)5/h10,13,17,19-22,29H,7-9,11-12H2,1-6H3

InChI Key

HDDNZVWBRRAOGK-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
Myrospermum frutescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Tricarboxylic acid or derivatives
Ketal
2-furanone
Cyclic alcohol
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.56	ALOGPS
logP	2.39	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	13.79	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	117.6 m³·mol⁻¹	ChemAxon
Polarizability	49.64 Å³	ChemAxon
Number of Rings	4	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

72831081

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate (NP0193163)

MOL for NP0193163 ([5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate)

3D MOL for NP0193163 ([5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate)

3D SDF for NP0193163 ([5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate)

3D-SDF for NP0193163 ([5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate)

PDB for NP0193163 ([5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate)

3D PDB for NP0193163 ([5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate)

SMILES for NP0193163 ([5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate)

INCHI for NP0193163 ([5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate)

Structure for NP0193163 ([5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate)

3D Structure for NP0193163 ([5-(acetyloxy)-6-hydroxy-10a-methoxy-4,7,11b-trimethyl-9-oxo-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-4-yl]methyl acetate)