NP-MRD: Showing NP-Card for dihydrogranaticin (NP0164253)

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Record Information

Version

2.0

Created at

2022-09-02 23:05:55 UTC

Updated at

2022-09-02 23:05:56 UTC

NP-MRD ID

NP0164253

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dihydrogranaticin

Description

CHEBI:81705 Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. CHEBI:81705 Is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. dihydrogranaticin is found in Streptomyces thermoviolaceus. Based on a literature review very few articles have been published on CHEBI:81705.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032201052D          

 32 36  0  0  1  0            999 V2000
    5.5693    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2837    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2837   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9982   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7127   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4272   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7127    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5680   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5680    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1465    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2825    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.6875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3351    0.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  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  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 24 32  1  6  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
    2.9898   -2.6522    1.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911   -1.5970    0.3276 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1488   -0.6736    0.9276 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542    0.3539    0.1223 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9362    0.1103   -0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9575   -0.0411    0.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5754    0.0463    1.7840 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2896   -0.2705    0.3232 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5829    0.7977   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2193    0.3514   -0.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0585   -0.7999   -0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173   -1.2525    0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5478   -2.3398    0.8620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4401   -0.4092   -0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7160   -0.8370    0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0239   -1.9954    0.8322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7504   -0.0053   -0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5596    1.1968   -0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865    1.6483   -1.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2076    2.8444   -1.6966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2343    0.8180   -0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1092    1.2345   -1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3264    2.3206   -1.5727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8104    1.9460   -1.0871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6797    1.0164   -1.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8325   -0.3416   -1.2764 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0533   -1.2316   -2.0459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2011   -0.3273    0.1007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3919   -1.4520    0.8269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7543    0.9257    0.7842 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2348    0.9275    2.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4707    2.0865    0.1337 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390   -3.5610    0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4432   -2.2500    2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9946   -2.9833    1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7165   -2.0587   -0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7034    1.2464    0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8676   -0.8890   -0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2366    0.9175   -1.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5957   -0.7824   -0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6235    1.8870   -1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724    0.3130   -1.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5562   -2.7593    1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533    3.3571   -2.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488    2.8913   -1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2089    0.9578   -2.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6951    1.4954   -1.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8900   -0.6750   -1.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9112   -0.8745   -2.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6848   -2.1900    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8637    0.7717    0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4470    1.7134    2.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8414   -0.0775    2.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0490    1.1515    2.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  8  1  0
  6  7  2  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  1
 28 30  1  0
 30 31  1  0
 30 32  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 11  2  1  0
 21 14  1  0
 22 10  1  0
 28 17  1  0
 32 24  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  6
  4 37  1  1
  5 38  1  0
  5 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 16 43  1  0
 24 45  1  6
 25 46  1  0
 25 47  1  0
 26 48  1  1
 27 49  1  0
 29 50  1  0
 30 51  1  1
 31 52  1  0
 31 53  1  0
 31 54  1  0
 20 44  1  0
M  END


  Mrv1652309032201052D          

 32 36  0  0  1  0            999 V2000
    5.5693    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2837    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2837   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9982   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7127   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4272   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7127    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5680   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5680    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1465    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2825    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.6875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3351    0.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  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  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 24 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0164253

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](CC(O)=O)CC2=C1C(=O)C1=C(O)C3=C([C@H]4C[C@@H](O)[C@]3(O)[C@@H](C)O4)C(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O10/c1-6-13-9(3-8(31-6)4-12(24)25)18(26)15-16(19(13)27)21(29)17-14(20(15)28)10-5-11(23)22(17,30)7(2)32-10/h6-8,10-11,23,28-30H,3-5H2,1-2H3,(H,24,25)/t6-,7+,8+,10+,11+,22+/m0/s1

> <INCHI_KEY>
YJRUVYZQSJVSCI-GNHMSDOPSA-N

> <FORMULA>
C22H22O10

> <MOLECULAR_WEIGHT>
446.408

> <EXACT_MASS>
446.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.61647697927089

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S,7S,9R,16R,18R,19R)-1,3,14,19-tetrahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0^{2,15}.0^{4,13}.0^{6,11}]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
0.7133286469999994

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.111990305673428

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1785605535356334

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4054394172716025

> <JCHEM_POLAR_SURFACE_AREA>
170.81999999999996

> <JCHEM_REFRACTIVITY>
107.44819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,7S,9R,16R,18R,19R)-1,3,14,19-tetrahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0^{2,15}.0^{4,13}.0^{6,11}]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      10.396   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.396   2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.730   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.730  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.063  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.397  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      15.731  -0.770   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      14.397   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.396  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.062   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.062   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.729   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.729   3.850   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.395   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.061   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.061   3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.728   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.728   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.061  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.061  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.395   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.729  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.729  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.394  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.060  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.060   1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.273   2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.394   2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.394   3.850   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.137   1.283   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.625   0.990   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.137   0.257   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   28                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14   22                                                  
CONECT   22   21   10   23                                                  
CONECT   23   22                                                            
CONECT   24   18   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   17   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   24                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₁₀

Average Mass

446.4080 Da

Monoisotopic Mass

446.12130 Da

IUPAC Name

2-[(1S,7S,9R,16R,18R,19R)-1,3,14,19-tetrahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0^{2,15}.0^{4,13}.0^{6,11}]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid

Traditional Name

[(1S,7S,9R,16R,18R,19R)-1,3,14,19-tetrahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0^{2,15}.0^{4,13}.0^{6,11}]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](CC(O)=O)CC2=C1C(=O)C1=C(O)C3=C([C@H]4C[C@@H](O)[C@]3(O)[C@@H](C)O4)C(O)=C1C2=O

InChI Identifier

InChI=1S/C22H22O10/c1-6-13-9(3-8(31-6)4-12(24)25)18(26)15-16(19(13)27)21(29)17-14(20(15)28)10-5-11(23)22(17,30)7(2)32-10/h6-8,10-11,23,28-30H,3-5H2,1-2H3,(H,24,25)/t6-,7+,8+,10+,11+,22+/m0/s1

InChI Key

YJRUVYZQSJVSCI-GNHMSDOPSA-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
Streptomyces thermoviolaceus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
1,4-anthraquinone
Benzoisochromanequinone
Isochromanequinone
Naphthopyranone
Naphthopyran
Benzopyran
Isochromane
Naphthalene
Tetralin
2-benzopyran
Quinone
Aryl ketone
Pyranone
Pyran
Oxane
Tertiary alcohol
Vinylogous acid
Secondary alcohol
1,2-diol
Ketone
Oxacycle
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxide
Carbonyl group
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthraquinone (CHEBI:81705 )

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	0.31	ALOGPS
logP	0.71	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	107.45 m³·mol⁻¹	ChemAxon
Polarizability	43.62 Å³	ChemAxon
Number of Rings	5	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

30791368

KEGG Compound ID

C18359

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

136064474

PDB ID

Not Available

ChEBI ID

81705

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for dihydrogranaticin (NP0164253)

MOL for NP0164253 (dihydrogranaticin)

3D MOL for NP0164253 (dihydrogranaticin)

3D SDF for NP0164253 (dihydrogranaticin)

3D-SDF for NP0164253 (dihydrogranaticin)

PDB for NP0164253 (dihydrogranaticin)

3D PDB for NP0164253 (dihydrogranaticin)

SMILES for NP0164253 (dihydrogranaticin)

INCHI for NP0164253 (dihydrogranaticin)

Structure for NP0164253 (dihydrogranaticin)

3D Structure for NP0164253 (dihydrogranaticin)