NP-MRD: Showing NP-Card for 4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one (NP0253256)

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Record Information

Version

2.0

Created at

2022-09-07 17:04:52 UTC

Updated at

2022-09-07 17:04:52 UTC

NP-MRD ID

NP0253256

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one

Description

FERRUGININ C belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. 4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one is found in Vismia macrophylla. 4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one was first documented in 2003 (PMID: 12828475). Based on a literature review very few articles have been published on FERRUGININ C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072219042D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072219042D          

 39 41  0  0  0  0            999 V2000
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    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0421   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3242   -1.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367   -1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4189   -2.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670   -1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151   -0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4454   -1.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1633   -2.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2579   -1.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 13 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  2  0  0  0  0
  9 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 27 38  1  0  0  0  0
  6 38  1  0  0  0  0
 38 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0253256

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(C)C=C(O)C2=C(O)C3=C(C=C12)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)=C3O

> <INCHI_IDENTIFIER>
InChI=1S/C35H44O4/c1-20(2)10-12-25-24(9)18-29(36)30-27(25)19-28-31(33(30)38)32(37)26(13-11-21(3)4)34(39)35(28,16-14-22(5)6)17-15-23(7)8/h10-11,14-15,18-19,36-38H,12-13,16-17H2,1-9H3

> <INCHI_KEY>
SJEQJMPZRHDLDB-UHFFFAOYSA-N

> <FORMULA>
C35H44O4

> <MOLECULAR_WEIGHT>
528.733

> <EXACT_MASS>
528.323959897

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
61.80883619531668

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)-1,2-dihydroanthracen-2-one

> <JCHEM_LOGP>
9.337581289000003

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.297263583876973

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.223316422858009

> <JCHEM_PKA_STRONGEST_BASIC>
-5.92315138842183

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
167.90060000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   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  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.000   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   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.679  -1.950   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.205  -3.397   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.722  -3.664   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.249  -5.111   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.712  -2.485   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.658  -1.950   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.175  -1.682   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.165  -2.862   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.638  -4.309   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.681  -2.595   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       9.336  -0.770   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   38                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   25                                                  
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   13   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   12   25                                                  
CONECT   25   24    9   26                                                  
CONECT   26   25                                                            
CONECT   27   10   28   33   38                                             
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   27   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   27    6   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₄₄O₄

Average Mass

528.7330 Da

Monoisotopic Mass

528.32396 Da

IUPAC Name

4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)-1,2-dihydroanthracen-2-one

Traditional Name

4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(C)C=C(O)C2=C(O)C3=C(C=C12)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)=C3O

InChI Identifier

InChI=1S/C35H44O4/c1-20(2)10-12-25-24(9)18-29(36)30-27(25)19-28-31(33(30)38)32(37)26(13-11-21(3)4)34(39)35(28,16-14-22(5)6)17-15-23(7)8/h10-11,14-15,18-19,36-38H,12-13,16-17H2,1-9H3

InChI Key

SJEQJMPZRHDLDB-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
Vismia macrophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Not Available

Direct Parent

Anthracenes

Alternative Parents

Substituents

Anthracene
1-naphthol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Ketone
Cyclic ketone
Enol
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	9.34	ChemAxon
pKa (Strongest Acidic)	6.22	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	167.9 m³·mol⁻¹	ChemAxon
Polarizability	61.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

C00044758

Chemspider ID

8612396

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10436972

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hussein AA, Bozzi B, Correa M, Capson TL, Kursar TA, Coley PD, Solis PN, Gupta MP: Bioactive constituents from three Vismia species. J Nat Prod. 2003 Jun;66(6):858-60. doi: 10.1021/np020566w. [PubMed:12828475 ]
LOTUS database [Link]

Showing NP-Card for 4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one (NP0253256)

MOL for NP0253256 (4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one)

3D MOL for NP0253256 (4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one)

3D SDF for NP0253256 (4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one)

3D-SDF for NP0253256 (4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one)

PDB for NP0253256 (4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one)

3D PDB for NP0253256 (4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one)

SMILES for NP0253256 (4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one)

INCHI for NP0253256 (4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one)

Structure for NP0253256 (4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one)

3D Structure for NP0253256 (4,5,10-trihydroxy-7-methyl-1,1,3,8-tetrakis(3-methylbut-2-en-1-yl)anthracen-2-one)