NP-MRD: Showing NP-Card for (3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one (NP0226745)

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Record Information

Version

2.0

Created at

2022-09-06 05:52:55 UTC

Updated at

2022-09-06 05:52:56 UTC

NP-MRD ID

NP0226745

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one

Description

Marginatone 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. (3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one was first documented in 2012 (PMID: 22676376). Based on a literature review very few articles have been published on Marginatone.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062207522D          

 22 25  0  0  1  0            999 V2000
    1.8641    0.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5458    0.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8548   -2.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  2  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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 21  1  6  0  0  0
  7 22  1  0  0  0  0
 12 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226745

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC(=O)C2=C1OC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-18(2)8-5-9-19(3)15(18)6-10-20(4)16(19)12-14(21)13-7-11-22-17(13)20/h7,11,15-16H,5-6,8-10,12H2,1-4H3/t15-,16+,19-,20+/m0/s1

> <INCHI_KEY>
FTDARKDISPGDGI-ACZWYYKOSA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.442

> <EXACT_MASS>
300.208930142

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
35.288418820862205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,7S,10R)-2,6,6,10-tetramethyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-11(15),13-dien-16-one

> <JCHEM_LOGP>
4.527431008666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.169470697118172

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0486617910031915

> <JCHEM_POLAR_SURFACE_AREA>
30.21

> <JCHEM_REFRACTIVITY>
87.68549999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,7S,10R)-2,6,6,10-tetramethyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-11(15),13-dien-16-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       3.480   0.682   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.342   1.354   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.352   0.273   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.091  -0.231   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.929  -5.250   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   22                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   22                                             
CONECT   13   12                                                            
CONECT   14   12   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21    7   12                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₂

Average Mass

300.4420 Da

Monoisotopic Mass

300.20893 Da

IUPAC Name

(1R,2S,7S,10R)-2,6,6,10-tetramethyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-11(15),13-dien-16-one

Traditional Name

(1R,2S,7S,10R)-2,6,6,10-tetramethyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-11(15),13-dien-16-one

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC(=O)C2=C1OC=C2

InChI Identifier

InChI=1S/C20H28O2/c1-18(2)8-5-9-19(3)15(18)6-10-20(4)16(19)12-14(21)13-7-11-22-17(13)20/h7,11,15-16H,5-6,8-10,12H2,1-4H3/t15-,16+,19-,20+/m0/s1

InChI Key

FTDARKDISPGDGI-ACZWYYKOSA-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

Not Available

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
Benzofuran
Aryl alkyl ketone
Aryl ketone
Heteroaromatic compound
Furan
Ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	4.53	ChemAxon
pKa (Strongest Acidic)	15.17	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.21 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.69 m³·mol⁻¹	ChemAxon
Polarizability	35.29 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

9601446

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11426570

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gris A, Cabedo N, Navarro I, de Alfonso I, Agullo C, Abad-Somovilla A: General diastereoselective synthetic approach toward isospongian diterpenes. Synthesis of (-)-marginatafuran, (-)-marginatone, and (-)-20-acetoxymarginatone. J Org Chem. 2012 Jul 6;77(13):5664-80. doi: 10.1021/jo3008034. Epub 2012 Jun 18. [PubMed:22676376 ]
LOTUS database [Link]

Showing NP-Card for (3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one (NP0226745)

MOL for NP0226745 ((3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one)

3D MOL for NP0226745 ((3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one)

3D SDF for NP0226745 ((3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one)

3D-SDF for NP0226745 ((3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one)

PDB for NP0226745 ((3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one)

3D PDB for NP0226745 ((3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one)

SMILES for NP0226745 ((3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one)

INCHI for NP0226745 ((3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one)

Structure for NP0226745 ((3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one)

3D Structure for NP0226745 ((3br,5as,9as,9br)-3b,6,6,9a-tetramethyl-4h,5h,5ah,7h,8h,9h,9bh,10h-phenanthro[1,2-b]furan-11-one)