NP-MRD: Showing NP-Card for Rubrofusarin (NP0026925)

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Record Information

Version

2.0

Created at

2021-06-19 18:41:24 UTC

Updated at

2021-06-29 23:52:45 UTC

NP-MRD ID

NP0026925

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rubrofusarin

Provided By

JEOL Database JEOL Logo

Description

Rubrofusarin is also known as NSC 258316. Rubrofusarin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Rubrofusarin is found in Senna longiracemosa, Senna macranthera, Senna obliqua and Senna obtusifolia. Rubrofusarin was first documented in 2010 (PMID: 20506081). Based on a literature review a small amount of articles have been published on rubrofusarin (PMID: 22377027) (PMID: 20543064) (PMID: 21296881) (PMID: 23557488).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120413D          

 32 34  0  0  0  0            999 V2000
   -1.0468    2.5261    3.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875    1.5004    3.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1306    1.1413    1.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960    1.6840    0.7413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1696    1.2147   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384    1.8088   -1.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    0.1922   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1582   -0.3223   -2.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415    0.2100   -3.1283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1177   -1.3371   -2.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5131   -1.8818   -3.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130   -1.4636   -4.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289   -2.9438   -3.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0405   -3.3611   -2.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780   -4.4372   -2.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6709   -2.8504   -1.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243   -1.8568   -0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3781   -1.3682    0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -0.3510    0.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    0.1309    1.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    3.4667    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0409    2.2202    3.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042    2.6948    4.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2396    2.4691    0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5108    1.3837   -2.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026   -0.2477   -3.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8218   -3.3467   -4.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7056   -5.2754   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9858   -4.0506   -1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3520   -4.8230   -3.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -1.7878    1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610   -0.2823    2.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 17  2  0  0  0  0
 13 14  2  0  0  0  0
 13 11  1  0  0  0  0
  7  5  1  0  0  0  0
 19 20  1  0  0  0  0
 20  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 14 16  1  0  0  0  0
  5  6  1  0  0  0  0
 10  8  1  0  0  0  0
  8  9  1  0  0  0  0
 17 18  1  0  0  0  0
 11 12  2  0  0  0  0
 18 19  2  0  0  0  0
 14 15  1  0  0  0  0
  7  8  2  0  0  0  0
  3  2  1  0  0  0  0
  7 19  1  0  0  0  0
  2  1  1  0  0  0  0
 13 27  1  0  0  0  0
 18 31  1  0  0  0  0
 20 32  1  0  0  0  0
  4 24  1  0  0  0  0
  6 25  1  0  0  0  0
  9 26  1  0  0  0  0
 15 28  1  0  0  0  0
 15 29  1  0  0  0  0
 15 30  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -1.0468    2.5261    3.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875    1.5004    3.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1306    1.1413    1.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960    1.6840    0.7413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1696    1.2147   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384    1.8088   -1.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    0.1922   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1582   -0.3223   -2.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415    0.2100   -3.1283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1177   -1.3371   -2.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5131   -1.8818   -3.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130   -1.4636   -4.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289   -2.9438   -3.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0405   -3.3611   -2.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780   -4.4372   -2.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6709   -2.8504   -1.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243   -1.8568   -0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3781   -1.3682    0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -0.3510    0.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    0.1309    1.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    3.4667    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0409    2.2202    3.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042    2.6948    4.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2396    2.4691    0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5108    1.3837   -2.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026   -0.2477   -3.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8218   -3.3467   -4.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7056   -5.2754   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9858   -4.0506   -1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3520   -4.8230   -3.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -1.7878    1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610   -0.2823    2.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 10 11  1  0
 10 17  2  0
 13 14  2  0
 13 11  1  0
  7  5  1  0
 19 20  1  0
 20  3  2  0
  3  4  1  0
  4  5  2  0
 14 16  1  0
  5  6  1  0
 10  8  1  0
  8  9  1  0
 17 18  1  0
 11 12  2  0
 18 19  2  0
 14 15  1  0
  7  8  2  0
  3  2  1  0
  7 19  1  0
  2  1  1  0
 13 27  1  0
 18 31  1  0
 20 32  1  0
  4 24  1  0
  6 25  1  0
  9 26  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END


  Mrv1652306192120413D          

 32 34  0  0  0  0            999 V2000
   -1.0468    2.5261    3.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875    1.5004    3.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1306    1.1413    1.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960    1.6840    0.7413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1696    1.2147   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384    1.8088   -1.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    0.1922   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1582   -0.3223   -2.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415    0.2100   -3.1283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1177   -1.3371   -2.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5131   -1.8818   -3.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130   -1.4636   -4.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289   -2.9438   -3.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0405   -3.3611   -2.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780   -4.4372   -2.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6709   -2.8504   -1.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243   -1.8568   -0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3781   -1.3682    0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -0.3510    0.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    0.1309    1.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    3.4667    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0409    2.2202    3.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042    2.6948    4.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2396    2.4691    0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5108    1.3837   -2.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026   -0.2477   -3.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8218   -3.3467   -4.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7056   -5.2754   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9858   -4.0506   -1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3520   -4.8230   -3.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -1.7878    1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610   -0.2823    2.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 17  2  0  0  0  0
 13 14  2  0  0  0  0
 13 11  1  0  0  0  0
  7  5  1  0  0  0  0
 19 20  1  0  0  0  0
 20  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 14 16  1  0  0  0  0
  5  6  1  0  0  0  0
 10  8  1  0  0  0  0
  8  9  1  0  0  0  0
 17 18  1  0  0  0  0
 11 12  2  0  0  0  0
 18 19  2  0  0  0  0
 14 15  1  0  0  0  0
  7  8  2  0  0  0  0
  3  2  1  0  0  0  0
  7 19  1  0  0  0  0
  2  1  1  0  0  0  0
 13 27  1  0  0  0  0
 18 31  1  0  0  0  0
 20 32  1  0  0  0  0
  4 24  1  0  0  0  0
  6 25  1  0  0  0  0
  9 26  1  0  0  0  0
 15 28  1  0  0  0  0
 15 29  1  0  0  0  0
 15 30  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026925

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(OC([H])([H])[H])=C([H])C2=C([H])C3=C(C(=O)C([H])=C(O3)C([H])([H])[H])C(O[H])=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c1-7-3-10(16)14-12(20-7)5-8-4-9(19-2)6-11(17)13(8)15(14)18/h3-6,17-18H,1-2H3

> <INCHI_KEY>
FPNKCZKRICBAKG-UHFFFAOYSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.2528

> <EXACT_MASS>
272.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.53139756332094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6-dihydroxy-8-methoxy-2-methyl-4H-benzo[g]chromen-4-one

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
2.7462281169999994

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.882416268638794

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.824094813972821

> <JCHEM_PKA_STRONGEST_BASIC>
-4.720657156866943

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
73.98240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rubrofusarin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -1.0468    2.5261    3.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875    1.5004    3.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1306    1.1413    1.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960    1.6840    0.7413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1696    1.2147   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384    1.8088   -1.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    0.1922   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1582   -0.3223   -2.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415    0.2100   -3.1283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1177   -1.3371   -2.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5131   -1.8818   -3.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130   -1.4636   -4.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289   -2.9438   -3.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0405   -3.3611   -2.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780   -4.4372   -2.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6709   -2.8504   -1.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243   -1.8568   -0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3781   -1.3682    0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -0.3510    0.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    0.1309    1.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    3.4667    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0409    2.2202    3.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042    2.6948    4.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2396    2.4691    0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5108    1.3837   -2.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026   -0.2477   -3.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8218   -3.3467   -4.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7056   -5.2754   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9858   -4.0506   -1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3520   -4.8230   -3.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -1.7878    1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610   -0.2823    2.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 10 11  1  0
 10 17  2  0
 13 14  2  0
 13 11  1  0
  7  5  1  0
 19 20  1  0
 20  3  2  0
  3  4  1  0
  4  5  2  0
 14 16  1  0
  5  6  1  0
 10  8  1  0
  8  9  1  0
 17 18  1  0
 11 12  2  0
 18 19  2  0
 14 15  1  0
  7  8  2  0
  3  2  1  0
  7 19  1  0
  2  1  1  0
 13 27  1  0
 18 31  1  0
 20 32  1  0
  4 24  1  0
  6 25  1  0
  9 26  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.047   2.526   3.386  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.088   1.500   3.158  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.131   1.141   1.856  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.496   1.684   0.741  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.170   1.215  -0.532  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.838   1.809  -1.573  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.788   0.192  -0.743  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.158  -0.322  -2.013  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.542   0.210  -3.128  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.118  -1.337  -2.130  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.513  -1.882  -3.435  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.013  -1.464  -4.473  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.529  -2.944  -3.438  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.040  -3.361  -2.272  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.078  -4.437  -2.189  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.671  -2.850  -1.037  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.724  -1.857  -0.995  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.378  -1.368   0.264  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.418  -0.351   0.404  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.080   0.131   1.680  0.00  0.00           C+0
HETATM   21  H   UNK     0      -0.738   3.467   2.918  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.041   2.220   3.044  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.104   2.695   4.466  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.240   2.469   0.820  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.511   1.384  -2.394  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.903  -0.248  -3.925  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.822  -3.347  -4.399  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.706  -5.275  -1.591  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.986  -4.051  -1.714  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.352  -4.823  -3.176  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.864  -1.788   1.143  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.561  -0.282   2.566  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    3    1                                                       
CONECT    3   20    4    2                                                  
CONECT    4    3    5   24                                                  
CONECT    5    7    4    6                                                  
CONECT    6    5   25                                                       
CONECT    7    5    8   19                                                  
CONECT    8   10    9    7                                                  
CONECT    9    8   26                                                       
CONECT   10   11   17    8                                                  
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   14   11   27                                                  
CONECT   14   13   16   15                                                  
CONECT   15   14   28   29   30                                             
CONECT   16   17   14                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17   19   31                                                  
CONECT   19   20   18    7                                                  
CONECT   20   19    3   32                                                  
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    4                                                            
CONECT   25    6                                                            
CONECT   26    9                                                            
CONECT   27   13                                                            
CONECT   28   15                                                            
CONECT   29   15                                                            
CONECT   30   15                                                            
CONECT   31   18                                                            
CONECT   32   20                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

RDKit          3D

32 34  0  0  0  0  0  0  0  0999 V2000
   -1.0468    2.5261    3.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875    1.5004    3.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1306    1.1413    1.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960    1.6840    0.7413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1696    1.2147   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384    1.8088   -1.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    0.1922   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1582   -0.3223   -2.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415    0.2100   -3.1283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1177   -1.3371   -2.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5131   -1.8818   -3.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130   -1.4636   -4.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289   -2.9438   -3.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0405   -3.3611   -2.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780   -4.4372   -2.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6709   -2.8504   -1.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243   -1.8568   -0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3781   -1.3682    0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -0.3510    0.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    0.1309    1.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    3.4667    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0409    2.2202    3.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042    2.6948    4.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2396    2.4691    0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5108    1.3837   -2.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026   -0.2477   -3.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8218   -3.3467   -4.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7056   -5.2754   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9858   -4.0506   -1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3520   -4.8230   -3.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -1.7878    1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610   -0.2823    2.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 10 11  1  0
 10 17  2  0
 13 14  2  0
 13 11  1  0
  7  5  1  0
 19 20  1  0
 20  3  2  0
  3  4  1  0
  4  5  2  0
 14 16  1  0
  5  6  1  0
 10  8  1  0
  8  9  1  0
 17 18  1  0
 11 12  2  0
 18 19  2  0
 14 15  1  0
  7  8  2  0
  3  2  1  0
  7 19  1  0
  2  1  1  0
 13 27  1  0
 18 31  1  0
 20 32  1  0
  4 24  1  0
  6 25  1  0
  9 26  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END

View in JSmol

Synonyms

Value	Source
NSC 258316	ChEBI
5,6-Dihydroxy-8-methoxy-2-methyl-4H-benzo(g)chromen-4-one	MeSH

Chemical Formula

C₁₅H₁₂O₅

Average Mass

272.2528 Da

Monoisotopic Mass

272.06847 Da

IUPAC Name

5,6-dihydroxy-8-methoxy-2-methyl-4H-benzo[g]chromen-4-one

Traditional Name

rubrofusarin

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(OC([H])([H])[H])=C([H])C2=C([H])C3=C(C(=O)C([H])=C(O3)C([H])([H])[H])C(O[H])=C12

InChI Identifier

InChI=1S/C15H12O5/c1-7-3-10(16)14-12(20-7)5-8-4-9(19-2)6-11(17)13(8)15(14)18/h3-6,17-18H,1-2H3

InChI Key

FPNKCZKRICBAKG-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cassia quinquangula	KNApSAcK Database	22123792
Cassia tora	KNApSAcK Database	22123792
Mangifera indica	KNApSAcK Database	22123792
Senna longiracemosa	LOTUS Database	35616633
Senna macranthera	LOTUS Database	35616633
Senna obliqua	JEOL database	Graham, J. G., et al, J. Nat. Prod. 67, 225 (2004)
Senna obtusifolia	LOTUS Database	35616633
Senna quinquangulata	KNApSAcK Database	22123792
Senna tora	KNApSAcK Database	22123792

Species Where Detected

Species Name	Source	Reference
Fusarium culmorum	KNApSAcK Database	22123792
Fusarium graminearum	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthopyranones. These are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Chromone
1-naphthol
Benzopyran
Naphthalene
1-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:8908 )
phenols (CHEBI:8908 )
polyketide (CHEBI:8908 )
benzochromenone (CHEBI:8908 )
Naphthopyrones (C09047 )

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	2.9	ALOGPS
logP	2.75	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.82	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.98 m³·mol⁻¹	ChemAxon
Polarizability	27.53 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0176658

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

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

8908

Good Scents ID

Not Available

References

General References

Huang HB, Feng XJ, Liu L, Chen B, Lu YJ, Ma L, She ZG, Lin YC: Three dimeric naphtho-gamma-pyrones from the mangrove endophytic fungus Aspergillus tubingensis isolated from Pongamia pinnata. Planta Med. 2010 Nov;76(16):1888-91. doi: 10.1055/s-0030-1249955. Epub 2010 May 26. [PubMed:20506081 ]
Shaaban M, Shaaban KA, Abdel-Aziz MS: Seven naphtho-gamma-pyrones from the marine-derived fungus Alternaria alternata: structure elucidation and biological properties. Org Med Chem Lett. 2012 Feb 29;2:6. doi: 10.1186/2191-2858-2-6. [PubMed:22377027 ]
Frandsen RJ, Albertsen KS, Stougaard P, Sorensen JL, Nielsen KF, Olsson S, Giese H: Methylenetetrahydrofolate reductase activity is involved in the plasma membrane redox system required for pigment biosynthesis in filamentous fungi. Eukaryot Cell. 2010 Aug;9(8):1225-35. doi: 10.1128/EC.00031-10. Epub 2010 Jun 11. [PubMed:20543064 ]
Frandsen RJ, Schutt C, Lund BW, Staerk D, Nielsen J, Olsson S, Giese H: Two novel classes of enzymes are required for the biosynthesis of aurofusarin in Fusarium graminearum. J Biol Chem. 2011 Mar 25;286(12):10419-28. doi: 10.1074/jbc.M110.179853. Epub 2011 Feb 4. [PubMed:21296881 ]
Rugbjerg P, Naesby M, Mortensen UH, Frandsen RJ: Reconstruction of the biosynthetic pathway for the core fungal polyketide scaffold rubrofusarin in Saccharomyces cerevisiae. Microb Cell Fact. 2013 Apr 4;12:31. doi: 10.1186/1475-2859-12-31. [PubMed:23557488 ]
Graham, J. G., et al. (2004). Graham, J. G., et al, J. Nat. Prod. 67, 225 (2004). J. Nat. Prod..

Showing NP-Card for Rubrofusarin (NP0026925)

MOL for NP0026925 (Rubrofusarin)

3D MOL for NP0026925 (Rubrofusarin)

3D SDF for NP0026925 (Rubrofusarin)

3D-SDF for NP0026925 (Rubrofusarin)

PDB for NP0026925 (Rubrofusarin)

3D PDB for NP0026925 (Rubrofusarin)

SMILES for NP0026925 (Rubrofusarin)

INCHI for NP0026925 (Rubrofusarin)

Structure for NP0026925 (Rubrofusarin)

3D Structure for NP0026925 (Rubrofusarin)