NP-MRD: Showing NP-Card for (12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione (NP0243267)

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Record Information

Version

2.0

Created at

2022-09-07 03:46:55 UTC

Updated at

2022-09-07 03:46:56 UTC

NP-MRD ID

NP0243267

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione

Description

Scleroderolide 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. (12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione is found in Gremmeniella abietina and Neosetophoma cerealis. (12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione was first documented in 2011 (PMID: 21103541). Based on a literature review a significant number of articles have been published on Scleroderolide (PMID: 26582262) (PMID: 29734036) (PMID: 33279250) (PMID: 32093426) (PMID: 25658054).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072205462D          

 24 27  0  0  1  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2380   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5353    0.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650    0.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  2 13  2  0  0  0  0
  7 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  6 24  1  0  0  0  0
M  END

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    1.4112    2.9835   -0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0684    1.6580   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4393    1.5193   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0259    0.2810   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950    0.1024   -0.1401 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152   -0.8268    0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8306   -0.7100    0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0467   -1.8226    0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3255   -1.6646    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0744   -2.8288    0.4106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8984   -0.4233    0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1137    0.6888    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2606    0.5447   -0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910    1.8420   -0.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2433    1.4526    0.0263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0454    2.0473   -1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424   -0.0061    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0643   -0.7484   -0.8694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9212   -0.3721    1.5550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431   -3.1487    0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9049   -4.1590    0.4617 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0927   -3.2519    0.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6683   -4.3862    0.3724 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8096   -2.0768    0.1389 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7779    3.0439   -1.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8311    3.2475    0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2304    3.7403   -0.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0377    2.4154   -0.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7741   -0.8215   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0695   -2.8709    0.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6276    1.9438    0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1315    1.9203   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8580    3.1511   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7636    1.6987   -2.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7936   -1.4370   -0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649   -0.1155   -1.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3657   -1.4152   -1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5901    0.4920    1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1364   -0.4071    2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5422   -1.2799    1.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 11  2  0
 11  9  1  0
  9 10  1  0
  9  8  2  0
  8 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 22 24  1  0
 24  6  1  0
  6  7  1  0
  7 13  2  0
 13  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
 11 17  1  0
 17 18  1  0
 17 19  1  0
 17 15  1  0
 13 12  1  0
  7  8  1  0
  4  6  2  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 15 31  1  1
 10 30  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  5 29  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
M  END


  Mrv1652309072205462D          

 24 27  0  0  1  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2380   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5353    0.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650    0.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  2 13  2  0  0  0  0
  7 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  6 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243267

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1OC2=C(C(O)=C3C(=O)C(=O)OC4=C3C2=C(C)C=C4O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-6-5-8(19)15-10-9(6)16-12(18(3,4)7(2)23-16)13(20)11(10)14(21)17(22)24-15/h5,7,19-20H,1-4H3/t7-/m0/s1

> <INCHI_KEY>
MYDJDVOVZVSVIE-ZETCQYMHSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.32

> <EXACT_MASS>
328.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.094045003763526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12S)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1(15),5,7,9(16),10(14)-pentaene-2,3-dione

> <JCHEM_LOGP>
4.791960946

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.604572654675453

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.375614077733102

> <JCHEM_PKA_STRONGEST_BASIC>
-4.776451491020045

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
85.25890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(12S)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1(15),5,7,9(16),10(14)-pentaene-2,3-dione

> <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       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.466  -2.786   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.371  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.911  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.466  -0.294   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.599   0.748   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.161   1.216   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   24                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    2    7                                                  
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    8   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    6                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₆

Average Mass

328.3200 Da

Monoisotopic Mass

328.09469 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1OC2=C(C(O)=C3C(=O)C(=O)OC4=C3C2=C(C)C=C4O)C1(C)C

InChI Identifier

InChI=1S/C18H16O6/c1-6-5-8(19)15-10-9(6)16-12(18(3,4)7(2)23-16)13(20)11(10)14(21)17(22)24-15/h5,7,19-20H,1-4H3/t7-/m0/s1

InChI Key

MYDJDVOVZVSVIE-ZETCQYMHSA-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
Gremmeniella abietina	LOTUS Database	35616633
Neosetophoma cerealis	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
2-naphthol
Benzopyran
Naphthalene
2-benzopyran
1-benzopyran
Coumaran
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
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

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

71044103

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13786694

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Elsebai MF, Kehraus S, Lindequist U, Sasse F, Shaaban S, Gutschow M, Josten M, Sahl HG, Konig GM: Antimicrobial phenalenone derivatives from the marine-derived fungus Coniothyrium cereale. Org Biomol Chem. 2011 Feb 7;9(3):802-8. doi: 10.1039/c0ob00625d. Epub 2010 Nov 22. [PubMed:21103541 ]
Intaraudom C, Nitthithanasilp S, Rachtawee P, Boonruangprapa T, Prabpai S, Kongsaeree P, Pittayakhajonwut P: Phenalenone derivatives and the unusual tricyclic sesterterpene acid from the marine fungus Lophiostoma bipolare BCC25910. Phytochemistry. 2015 Dec;120:19-27. doi: 10.1016/j.phytochem.2015.11.003. Epub 2015 Nov 12. [PubMed:26582262 ]
Li Q, Zhu R, Yi W, Chai W, Zhang Z, Lian XY: Peniciphenalenins A-F from the culture of a marine-associated fungus Penicillium sp. ZZ901. Phytochemistry. 2018 Aug;152:53-60. doi: 10.1016/j.phytochem.2018.04.021. Epub 2018 May 4. [PubMed:29734036 ]
Yang SQ, Mandi A, Li XM, Liu H, Li X, Balazs Kiraly S, Kurtan T, Wang BG: Separation and configurational assignment of stereoisomeric phenalenones from the marine mangrove-derived fungus Penicillium herquei MA-370. Bioorg Chem. 2021 Jan;106:104477. doi: 10.1016/j.bioorg.2020.104477. Epub 2020 Nov 18. [PubMed:33279250 ]
Macabeo APG, Pilapil LAE, Garcia KYM, Quimque MTJ, Phukhamsakda C, Cruz AJC, Hyde KD, Stadler M: Alpha-Glucosidase- and Lipase-Inhibitory Phenalenones from a New Species of Pseudolophiostoma Originating from Thailand. Molecules. 2020 Feb 20;25(4):965. doi: 10.3390/molecules25040965. [PubMed:32093426 ]
Wang L, Feng Y, Tian J, Xiang M, Sun J, Ding J, Yin WB, Stadler M, Che Y, Liu X: Farming of a defensive fungal mutualist by an attelabid weevil. ISME J. 2015 Aug;9(8):1793-801. doi: 10.1038/ismej.2014.263. Epub 2015 Feb 6. [PubMed:25658054 ]
LOTUS database [Link]

Showing NP-Card for (12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione (NP0243267)

MOL for NP0243267 ((12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione)

3D MOL for NP0243267 ((12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione)

3D SDF for NP0243267 ((12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione)

3D-SDF for NP0243267 ((12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione)

PDB for NP0243267 ((12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione)

3D PDB for NP0243267 ((12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione)

SMILES for NP0243267 ((12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione)

INCHI for NP0243267 ((12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione)

Structure for NP0243267 ((12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione)

3D Structure for NP0243267 ((12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione)