NP-MRD: Showing NP-Card for 7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid (NP0294659)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 03:18:45 UTC

Updated at

2022-09-10 03:18:45 UTC

NP-MRD ID

NP0294659

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid

Description

7-(4-Carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxo-9,10-dihydrophenanthrene-3-carboxylic acid belongs to the class of organic compounds known as phenanthraquinones. These are phenanthrene derivatives containing two ketone groups at position C9 and C10, respectively. 7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid is found in Tapinella atrotomentosa. 7-(4-Carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxo-9,10-dihydrophenanthrene-3-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191515002D          

 29 31  0  0  0  0            999 V2000
   -3.8230   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8230   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  2  1  4  0  0  0
  4  5  2  0  0  0  0
  6  5  1  4  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
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 12 27  1  0  0  0  0
 27 28  2  0  0  0  0
  8 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    6.9394   -0.1164    1.8199 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9128   -0.2108    0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1613   -0.3326   -0.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7263   -0.2088   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5119   -0.1081    0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0969    0.0182    1.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9006    0.1401    2.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566    0.2002    1.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5924   -0.5735    1.7567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6779   -0.5680    1.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6413   -1.3836    1.7961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9679    0.2403    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0618    1.0200   -0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3642    1.0066    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2784    1.8383   -0.3372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1779    1.9023   -1.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7700    2.6009   -1.8979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045    1.9283   -2.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7513    2.6689   -3.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5646    1.0840   -1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8158    1.1111   -2.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8605    0.3273   -1.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0922    0.4015   -2.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6148   -0.4989   -0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6120   -1.3606    0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3121   -2.0844    1.0946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9005   -1.4378   -0.3251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3488   -0.5315    0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3231    0.2369   -0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1992   -0.9130   -0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8918   -0.3034   -1.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7242   -0.1760   -0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9125    0.0095    2.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7784    0.2120    3.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7896   -1.2262    2.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4126   -1.9655    2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697    2.1313   -0.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0387    1.7505   -2.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9070   -0.0705   -1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7002   -1.1482    0.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -1.1774    0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 29  1  0
 29 28  2  0
 28 24  1  0
 24 25  1  0
 25 27  1  0
 25 26  2  0
 24 22  2  0
 22 23  1  0
 22 21  1  0
 21 20  2  0
 20 18  1  0
 18 19  2  0
 18 16  1  0
 16 17  2  0
 16 13  1  0
 13 14  2  0
 14 15  1  0
 14  8  1  0
 13 12  1  0
 20 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
 11 36  1  0
 28 41  1  0
 27 40  1  0
 23 39  1  0
 21 38  1  0
 15 37  1  0
M  END


  Mrv1533004191515002D          

 29 31  0  0  0  0            999 V2000
   -3.8230   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8230   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  2  1  4  0  0  0
  4  5  2  0  0  0  0
  6  5  1  4  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
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 12 27  1  0  0  0  0
 27 28  2  0  0  0  0
  8 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0294659

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C=CC=CC1=CC(O)=C2C3=CC(C(O)=O)=C(O)C=C3C(=O)C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H12O9/c21-12-7-10-9(6-11(12)20(28)29)15-13(22)5-8(3-1-2-4-14(23)24)17(25)16(15)19(27)18(10)26/h1-7,21-22,25H,(H,23,24)(H,28,29)

> <INCHI_KEY>
FBOUTZRGPQLFJG-UHFFFAOYSA-N

> <FORMULA>
C20H12O9

> <MOLECULAR_WEIGHT>
396.307

> <EXACT_MASS>
396.048131966

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
38.12102893635464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxo-9,10-dihydrophenanthrene-3-carboxylic acid

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
3.655649134999999

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.9050531294948305

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.273479579325238

> <JCHEM_PKA_STRONGEST_BASIC>
-5.658737654088051

> <JCHEM_POLAR_SURFACE_AREA>
169.42999999999998

> <JCHEM_REFRACTIVITY>
101.67039999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  O   UNK     0      -7.136  -7.851   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.366  -6.517   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -7.136  -5.184   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.826  -6.517   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.056  -5.184   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.516  -5.184   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.746  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.874  -1.183   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.494  -1.183   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.724   0.151   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.034  -1.183   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.034  -3.850   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.184  -7.851   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.104  -7.851   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.206  -6.517   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   27                                                  
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   15   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   13   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   12   28                                                  
CONECT   28   27    8   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
7-(4-Carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxo-9,10-dihydrophenanthrene-3-carboxylate	Generator

Chemical Formula

C₂₀H₁₂O₉

Average Mass

396.3070 Da

Monoisotopic Mass

396.04813 Da

IUPAC Name

7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxo-9,10-dihydrophenanthrene-3-carboxylic acid

Traditional Name

7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C=CC=CC1=CC(O)=C2C3=CC(C(O)=O)=C(O)C=C3C(=O)C(=O)C2=C1O

InChI Identifier

InChI=1S/C20H12O9/c21-12-7-10-9(6-11(12)20(28)29)15-13(22)5-8(3-1-2-4-14(23)24)17(25)16(15)19(27)18(10)26/h1-7,21-22,25H,(H,23,24)(H,28,29)

InChI Key

FBOUTZRGPQLFJG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tapinella atrotomentosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthraquinones. These are phenanthrene derivatives containing two ketone groups at position C9 and C10, respectively.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthraquinones

Direct Parent

Phenanthraquinones

Alternative Parents

Substituents

Phenanthraquinone
Hydrophenanthrene
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
1-naphthol
Hydroxybenzoic acid
Naphthalene
Salicylic acid or derivatives
Medium-chain fatty acid
Styrene
Quinone
Aryl ketone
O-quinone
1-hydroxy-2-unsubstituted benzenoid
Hydroxy fatty acid
Unsaturated fatty acid
Fatty acid
Fatty acyl
Dicarboxylic acid or derivatives
Vinylogous acid
Ketone
Carboxylic acid derivative
Polyol
Carboxylic acid
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.65	ALOGPS
logP	3.66	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.27	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	169.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.67 m³·mol⁻¹	ChemAxon
Polarizability	38.12 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid (NP0294659)

MOL for NP0294659 (7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid)

3D MOL for NP0294659 (7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid)

3D SDF for NP0294659 (7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid)

3D-SDF for NP0294659 (7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid)

PDB for NP0294659 (7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid)

3D PDB for NP0294659 (7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid)

SMILES for NP0294659 (7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid)

INCHI for NP0294659 (7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid)

Structure for NP0294659 (7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid)

3D Structure for NP0294659 (7-(4-carboxybuta-1,3-dien-1-yl)-2,5,8-trihydroxy-9,10-dioxophenanthrene-3-carboxylic acid)