NP-MRD: Showing NP-Card for (3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one (NP0326683)

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Record Information

Version

2.0

Created at

2022-09-12 08:29:53 UTC

Updated at

2022-09-12 08:29:53 UTC

NP-MRD ID

NP0326683

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one

Description

(3R)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-2H,3H,4H,11H-anthra[2,3-b]furan-4-one 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. (3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one is found in Harungana madagascariensis. Based on a literature review very few articles have been published on (3R)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-2H,3H,4H,11H-anthra[2,3-b]furan-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122210292D          

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  Mrv1652309122210292D          

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 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 12 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C2=C(OC1(C)C)C(CC=C(C)C)(CC=C(C)C)C1=C(C2=O)C(O)=C2C(O)=CC(C)=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O4/c1-16(2)9-11-30(12-10-17(3)4)21-15-20-13-18(5)14-22(31)24(20)27(33)25(21)26(32)23-19(6)29(7,8)34-28(23)30/h9-10,13-15,19,31,33H,11-12H2,1-8H3/t19-/m1/s1

> <INCHI_KEY>
AXIJTAQSMFBWGD-LJQANCHMSA-N

> <FORMULA>
C30H36O4

> <MOLECULAR_WEIGHT>
460.614

> <EXACT_MASS>
460.261359639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.98923352763833

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-2H,3H,4H,11H-anthra[2,3-b]furan-4-one

> <JCHEM_LOGP>
7.268195713000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.46574301863082

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.918676426369771

> <JCHEM_PKA_STRONGEST_BASIC>
-4.855538201540994

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
141.09769999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3H-anthra[2,3-b]furan-4-one

> <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      11.681  -2.595   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.165  -2.862   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.638  -4.309   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.175  -1.682   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.658  -1.950   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.679  -1.950   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.162  -1.682   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.172  -2.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.655  -2.595   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.699  -4.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.467   2.016   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.943   3.481   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.372   0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.516   1.800   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.516  -0.260   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.467  -0.476   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12   17                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   13   34                                                  
CONECT   13   12   14   29                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   27                                                  
CONECT   17   16    6   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19   27                                                  
CONECT   27   26   16   28                                                  
CONECT   28   27                                                            
CONECT   29   13   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   12                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆O₄

Average Mass

460.6140 Da

Monoisotopic Mass

460.26136 Da

IUPAC Name

(3R)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-2H,3H,4H,11H-anthra[2,3-b]furan-4-one

Traditional Name

(3R)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3H-anthra[2,3-b]furan-4-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1C2=C(OC1(C)C)C(CC=C(C)C)(CC=C(C)C)C1=C(C2=O)C(O)=C2C(O)=CC(C)=CC2=C1

InChI Identifier

InChI=1S/C30H36O4/c1-16(2)9-11-30(12-10-17(3)4)21-15-20-13-18(5)14-22(31)24(20)27(33)25(21)26(32)23-19(6)29(7,8)34-28(23)30/h9-10,13-15,19,31,33H,11-12H2,1-8H3/t19-/m1/s1

InChI Key

AXIJTAQSMFBWGD-LJQANCHMSA-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
Harungana madagascariensis	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
1-naphthol
Naphthalene
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Vinylogous ester
Vinylogous acid
Dihydrofuran
Ketone
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
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	7.27	ChemAxon
pKa (Strongest Acidic)	7.92	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	141.1 m³·mol⁻¹	ChemAxon
Polarizability	52.99 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

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

163097855

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one (NP0326683)

MOL for NP0326683 ((3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one)

3D MOL for NP0326683 ((3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one)

3D SDF for NP0326683 ((3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one)

3D-SDF for NP0326683 ((3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one)

PDB for NP0326683 ((3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one)

3D PDB for NP0326683 ((3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one)

SMILES for NP0326683 ((3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one)

INCHI for NP0326683 ((3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one)

Structure for NP0326683 ((3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one)

3D Structure for NP0326683 ((3r)-5,6-dihydroxy-2,2,3,8-tetramethyl-11,11-bis(3-methylbut-2-en-1-yl)-3h-anthra[2,3-b]furan-4-one)