NP-MRD: Showing NP-Card for 5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2h-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid (NP0318681)

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Record Information

Version

1.0

Created at

2022-09-11 19:19:14 UTC

Updated at

2022-09-11 19:19:15 UTC

NP-MRD ID

NP0318681

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2h-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid

Description

5-Hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2H,3H,6H,9H-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid 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. It was first documented in 2002 (PMID: 31593387). Based on a literature review a significant number of articles have been published on 5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2H,3H,6H,9H-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid (PMID: 27253005) (PMID: 27583328) (PMID: 36127157) (PMID: 36127156).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112221192D          

 30 32  0  0  0  0            999 V2000
    6.3850   -0.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950    0.3610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2150    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    1.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -1.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6504   -0.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1733   -0.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993   -1.4495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599   -0.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0725   -1.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7409   -1.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2669   -1.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0284   -2.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024   -3.2715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8418   -2.7737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1258   -1.0415    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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  4  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  9 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -6.4673    2.8119   -0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8460    2.0044   -0.2929 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1357    0.8092    0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3874    0.6804    0.7464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2002   -0.2824    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5267   -1.6196    0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0364   -0.0591   -0.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0967   -1.1522   -0.6826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8557   -1.0330    0.1246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9932   -2.1190   -0.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0589    0.1915   -0.2219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6630    1.4632    0.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2403    0.0285    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4937   -0.0987    1.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5175   -0.0970    2.8111 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135   -0.2364    2.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8333   -0.2399    1.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5480   -0.1089    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287    0.0284   -0.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7172    0.1712   -1.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7027    0.1916   -1.6483 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1276    1.4114   -2.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105   -0.1105   -0.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3331    0.0113   -2.1857 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0150   -0.2505   -0.5613 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0583   -0.2469   -1.5975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2747   -0.3759    0.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6165   -0.5086    1.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4809    0.6088    1.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2380   -0.3788    1.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5383   -0.5021    2.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9817   -0.1417    0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4866   -1.6485    1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7693   -2.0456    1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5983   -2.3503   -0.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7839    0.9159   -0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5738   -2.1507   -0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8866   -1.2771   -1.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0147   -1.1247    1.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2881   -2.3873   -1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9766    2.1922   -0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9400    1.9210    1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5324    1.1891    0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3411   -0.1909    3.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0547   -0.3399    3.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0197   -0.6856   -2.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6112    1.3149   -3.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6995    2.3484   -1.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1889    1.4741   -2.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0127   -0.6793   -1.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2828    0.7867   -1.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7694   -0.8540   -2.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1107    1.3513    1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4598    0.2362    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5769    1.1535    0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 27  1  0
 27 25  2  0
 25 26  1  0
 25 23  1  0
 23 24  2  0
 23 18  1  0
 18 17  2  0
 17 16  1  0
 16 14  2  0
 14 15  1  0
 14 13  1  0
 13 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 11  1  0
 11 12  1  1
 11  9  1  0
  9 10  1  0
  9  8  1  0
  8  7  1  0
  7  5  2  0
  5  6  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
 17 30  1  0
 30 31  2  0
 30 27  1  0
 19 18  1  0
 11 13  1  0
 29 53  1  0
 29 54  1  0
 29 55  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 16 45  1  0
 15 44  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 22 49  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
  9 39  1  1
 10 40  1  0
  8 37  1  0
  8 38  1  0
  7 36  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  4 32  1  0
  2  1  1  0
M  END


  Mrv1652309112221192D          

 30 32  0  0  0  0            999 V2000
    6.3850   -0.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950    0.3610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2150    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    1.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -1.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6504   -0.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1733   -0.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993   -1.4495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599   -0.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0725   -1.7249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7409   -1.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2669   -1.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0284   -2.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024   -3.2715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8418   -2.7737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1258   -1.0415    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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  4  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  9 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0318681

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(=O)C2=C(C=C(O)C3=C2OC(C)C3(C)C(O)CC=C(C)C(O)=N)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H25NO7/c1-9(21(23)28)6-7-14(25)22(4)11(3)30-20-15-12(8-13(24)16(20)22)18(27)19(29-5)10(2)17(15)26/h6,8,11,14,24-25H,7H2,1-5H3,(H2,23,28)

> <INCHI_KEY>
GBBLKHXBUPVKJV-UHFFFAOYSA-N

> <FORMULA>
C22H25NO7

> <MOLECULAR_WEIGHT>
415.442

> <EXACT_MASS>
415.163102149

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.819209031299046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2H,3H,6H,9H-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid

> <JCHEM_LOGP>
-0.7893984719151428

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.7301422854433675

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6137378902866519

> <JCHEM_PKA_STRONGEST_BASIC>
11.714404648368276

> <JCHEM_POLAR_SURFACE_AREA>
137.14000000000001

> <JCHEM_REFRACTIVITY>
122.09519999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2H-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      11.919  -0.683   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.191   0.674   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.735   3.388   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.384   2.127   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.656   3.484   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.139  -3.109   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.039   2.042   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.614   1.460   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.305   2.271   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.727  -0.076   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.214  -0.365   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.190  -1.519   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.172  -2.706   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.672  -1.776   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.135  -3.220   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.383  -3.477   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.365  -2.291   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.920  -4.920   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      -0.938  -6.107   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0      -3.438  -5.178   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.568  -1.944   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10   29                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   13   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    9    3   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
5-Hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2H,3H,6H,9H-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidate	Generator

Chemical Formula

C₂₂H₂₅NO₇

Average Mass

415.4420 Da

Monoisotopic Mass

415.16310 Da

IUPAC Name

5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2H,3H,6H,9H-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid

Traditional Name

5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2H-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)C2=C(C=C(O)C3=C2OC(C)C3(C)C(O)CC=C(C)C(O)=N)C1=O

InChI Identifier

InChI=1S/C22H25NO7/c1-9(21(23)28)6-7-14(25)22(4)11(3)30-20-15-12(8-13(24)16(20)22)18(27)19(29-5)10(2)17(15)26/h6,8,11,14,24-25H,7H2,1-5H3,(H2,23,28)

InChI Key

GBBLKHXBUPVKJV-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
Naphthoquinone
Naphthalene
Coumaran
Aryl ketone
Quinone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Vinylogous ester
Ketone
Secondary alcohol
Ether
Carboximidic acid derivative
Carboximidic acid
Oxacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organic nitrogen 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
logP	-0.79	ChemAxon
pKa (Strongest Acidic)	0.61	ChemAxon
pKa (Strongest Basic)	11.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	137.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.1 m³·mol⁻¹	ChemAxon
Polarizability	43.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76033994

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Authors unspecified: Childhood Esophageal Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31593387 ]
Authors unspecified: Financial Toxicity and Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:27583328 ]
Gadot R, Najera R, Hirani S, Anand A, Storch E, Goodman WK, Shofty B, Sheth SA: Efficacy of deep brain stimulation for treatment-resistant obsessive-compulsive disorder: systematic review and meta-analysis. J Neurol Neurosurg Psychiatry. 2022 Sep 20. pii: jnnp-2021-328738. doi: 10.1136/jnnp-2021-328738. [PubMed:36127157 ]
Koggel LM, Lantinga MA, Buchner FL, Drenth JPH, Frankema JS, Heeregrave EJ, Heringa M, Numans ME, Siersema PD: Predictors for inappropriate proton pump inhibitor use: observational study in primary care. Br J Gen Pract. 2022 Jun 24. pii: BJGP.2022.0178. doi: 10.3399/BJGP.2022.0178. [PubMed:36127156 ]
LOTUS database [Link]

Showing NP-Card for 5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2h-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid (NP0318681)

MOL for NP0318681 (5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2h-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid)

3D MOL for NP0318681 (5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2h-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid)

3D SDF for NP0318681 (5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2h-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid)

3D-SDF for NP0318681 (5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2h-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid)

PDB for NP0318681 (5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2h-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid)

3D PDB for NP0318681 (5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2h-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid)

SMILES for NP0318681 (5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2h-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid)

INCHI for NP0318681 (5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2h-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid)

Structure for NP0318681 (5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2h-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid)

3D Structure for NP0318681 (5-hydroxy-5-{4-hydroxy-7-methoxy-2,3,8-trimethyl-6,9-dioxo-2h-naphtho[1,2-b]furan-3-yl}-2-methylpent-2-enimidic acid)