NP-MRD: Showing NP-Card for 4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1h,4h,5h,5ah,7h,8h,9h-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate (NP0272449)

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Record Information

Version

2.0

Created at

2022-09-08 19:04:47 UTC

Updated at

2022-09-08 19:04:48 UTC

NP-MRD ID

NP0272449

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1h,4h,5h,5ah,7h,8h,9h-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate

Description

4-Hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1H,3H,4H,5H,5aH,6H,7H,8H,9H,9aH-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate 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. Based on a literature review very few articles have been published on 4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1H,3H,4H,5H,5aH,6H,7H,8H,9H,9aH-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082221042D          

 31 34  0  0  0  0            999 V2000
    0.2729   -1.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2075   -2.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5924   -2.9094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435   -0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -1.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -1.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440   -1.8107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -0.4553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228   -2.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5574   -2.9030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982   -2.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9082   -2.9545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428   -3.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1674   -3.6300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -4.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3874   -5.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9974   -5.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1728   -5.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7828   -6.5637    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.2174   -7.2650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0418   -6.5895    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.7382   -5.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282   -4.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -1.5262    0.0000 C   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  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  2  0  0  0  0
 22 30  1  0  0  0  0
 18 31  1  0  0  0  0
  2 31  1  0  0  0  0
  8 31  1  0  0  0  0
M  CHG  2  26   1  28  -1
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
   -1.0197   -2.5272   -0.8569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9648   -1.4759   -0.3227 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0492   -1.3213   -1.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7072   -2.5626   -1.5837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5685   -2.0774    0.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4696   -1.0988    1.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538    0.2776    1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1070    0.8223    0.6699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0371    1.5688   -0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801    1.9113    1.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762    1.5948    2.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2036    2.7974    2.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1747    2.8371    3.5512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5809    3.8552    2.3243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4145    3.4133    1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1345    0.1644    2.0912 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5050    0.1951    2.4719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0076   -0.4532    0.7217 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1722   -0.1067    0.0269 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1975   -0.9694   -0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0232   -2.1566    0.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3823   -0.5320   -1.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4153   -1.3681   -1.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5010   -0.8673   -2.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5886    0.4629   -2.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6851    1.0015   -3.1235 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.7166    2.1951   -3.4230 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7237    0.1946   -3.4763 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.5408    1.3132   -2.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4810    0.7912   -1.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567   -0.1670   -0.0168 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6226   -3.1995   -0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2305   -2.0923   -1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5965   -3.2163   -1.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6986   -1.0111   -2.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8777   -0.6970   -0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2316   -2.4416   -2.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7793   -2.4870    1.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1881   -2.9393    0.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5063   -1.1187    1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270   -1.5086    2.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4921    0.4342    2.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8810    0.9484    1.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0925    1.4863   -0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7894    1.3441   -1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7889    2.6402   -0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4775    3.6382    1.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0663    3.8324    0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305   -0.4223    2.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950    0.5158    3.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0581   -1.5482    0.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3540   -2.4162   -1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3269   -1.5083   -2.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6046    2.3617   -2.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6675    1.4748   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9816    0.2180   -1.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 31  1  0
 31 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 29  1  0
 29 30  2  0
 25 26  1  0
 26 28  1  0
 26 27  2  0
 18 16  1  0
 16 17  1  0
 16 11  1  0
 11 10  2  0
 10 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  2  0
 31  2  1  0
 30 22  1  0
 12 11  1  0
 10  8  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  0
  7 43  1  0
  9 44  1  0
  9 45  1  0
  9 46  1  0
 31 56  1  6
 18 51  1  1
 23 52  1  0
 24 53  1  0
 29 54  1  0
 30 55  1  0
 16 49  1  1
 17 50  1  0
 15 47  1  0
 15 48  1  0
M  CHG  2  26   1  28  -1
M  END


  Mrv1652309082221042D          

 31 34  0  0  0  0            999 V2000
    0.2729   -1.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2075   -2.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5924   -2.9094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435   -0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -1.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -1.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440   -1.8107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -0.4553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228   -2.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5574   -2.9030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982   -2.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9082   -2.9545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428   -3.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1674   -3.6300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -4.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3874   -5.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9974   -5.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1728   -5.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7828   -6.5637    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.2174   -7.2650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0418   -6.5895    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.7382   -5.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282   -4.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -1.5262    0.0000 C   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  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  2  0  0  0  0
 22 30  1  0  0  0  0
 18 31  1  0  0  0  0
  2 31  1  0  0  0  0
  8 31  1  0  0  0  0
M  CHG  2  26   1  28  -1
M  END
> <DATABASE_ID>
NP0272449

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(CO)CCCC2(C)C1C(OC(=O)C1=CC=C(C=C1)[N+]([O-])=O)C(O)C1=C2COC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H25NO8/c1-21(11-24)8-3-9-22(2)14-10-30-20(27)15(14)16(25)17(18(21)22)31-19(26)12-4-6-13(7-5-12)23(28)29/h4-7,16-18,24-25H,3,8-11H2,1-2H3

> <INCHI_KEY>
UQNYLSVKARJQKB-UHFFFAOYSA-N

> <FORMULA>
C22H25NO8

> <MOLECULAR_WEIGHT>
431.441

> <EXACT_MASS>
431.158016769

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.020959862268924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1H,3H,4H,5H,5aH,6H,7H,8H,9H,9aH-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate

> <JCHEM_LOGP>
2.4142536706666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.502337293097426

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.723496198417969

> <JCHEM_PKA_STRONGEST_BASIC>
-2.753312667913419

> <JCHEM_POLAR_SURFACE_AREA>
136.20000000000002

> <JCHEM_REFRACTIVITY>
107.99929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1H,4H,5H,5aH,7H,8H,9H-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       0.509  -3.469   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.939  -2.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.254  -4.405   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.106  -5.431   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.128  -1.588   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.856  -0.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.395  -0.183   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.207  -1.492   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.935  -0.135   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.746  -1.444   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.557  -2.753   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.053  -2.386   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.229  -3.380   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.166  -0.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.740  -0.268   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.829  -4.110   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.640  -5.419   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.290  -4.158   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.562  -5.515   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.373  -6.824   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.912  -6.776   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.645  -8.181   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.456  -9.490   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.729 -10.847   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.189 -10.895   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       1.461 -12.252   0.000  0.00  0.00           N+1
HETATM   27  O   UNK     0       2.273 -13.561   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.078 -12.300   0.000  0.00  0.00           O-1
HETATM   29  C   UNK     0       1.378  -9.586   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.106  -8.229   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.479  -2.849   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5   31                                             
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   31                                             
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   10                                                       
CONECT   16   11   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   30                                                       
CONECT   30   29   22                                                       
CONECT   31   18    2    8                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1H,3H,4H,5H,5ah,6H,7H,8H,9H,9ah-naphtho[1,2-c]furan-5-yl 4-nitrobenzoic acid	Generator

Chemical Formula

C₂₂H₂₅NO₈

Average Mass

431.4410 Da

Monoisotopic Mass

431.15802 Da

IUPAC Name

4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1H,3H,4H,5H,5aH,6H,7H,8H,9H,9aH-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate

Traditional Name

4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1H,4H,5H,5aH,7H,8H,9H-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate

CAS Registry Number

Not Available

SMILES

CC1(CO)CCCC2(C)C1C(OC(=O)C1=CC=C(C=C1)[N+]([O-])=O)C(O)C1=C2COC1=O

InChI Identifier

InChI=1S/C22H25NO8/c1-21(11-24)8-3-9-22(2)14-10-30-20(27)15(14)16(25)17(18(21)22)31-19(26)12-4-6-13(7-5-12)23(28)29/h4-7,16-18,24-25H,3,8-11H2,1-2H3

InChI Key

UQNYLSVKARJQKB-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

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
Nitrobenzoate
Benzoate ester
Benzoic acid or derivatives
Nitrobenzene
Nitroaromatic compound
Benzoyl
Monocyclic benzene moiety
2-furanone
Benzenoid
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
C-nitro compound
Carboxylic acid ester
Lactone
Secondary alcohol
Organic nitro compound
Carboxylic acid derivative
Oxacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Organic zwitterion
Primary alcohol
Organooxygen compound
Organonitrogen 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	2.41	ChemAxon
pKa (Strongest Acidic)	12.72	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	136.2 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	108 m³·mol⁻¹	ChemAxon
Polarizability	43.02 Å³	ChemAxon
Number of Rings	4	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

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

85448006

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1h,4h,5h,5ah,7h,8h,9h-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate (NP0272449)

MOL for NP0272449 (4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1h,4h,5h,5ah,7h,8h,9h-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate)

3D MOL for NP0272449 (4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1h,4h,5h,5ah,7h,8h,9h-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate)

3D SDF for NP0272449 (4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1h,4h,5h,5ah,7h,8h,9h-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate)

3D-SDF for NP0272449 (4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1h,4h,5h,5ah,7h,8h,9h-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate)

PDB for NP0272449 (4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1h,4h,5h,5ah,7h,8h,9h-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate)

3D PDB for NP0272449 (4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1h,4h,5h,5ah,7h,8h,9h-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate)

SMILES for NP0272449 (4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1h,4h,5h,5ah,7h,8h,9h-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate)

INCHI for NP0272449 (4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1h,4h,5h,5ah,7h,8h,9h-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate)

Structure for NP0272449 (4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1h,4h,5h,5ah,7h,8h,9h-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate)

3D Structure for NP0272449 (4-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-3-oxo-1h,4h,5h,5ah,7h,8h,9h-naphtho[1,2-c]furan-5-yl 4-nitrobenzoate)