NP-MRD: Showing NP-Card for [(7s,9r,18r)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid (NP0213066)

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Record Information

Version

2.0

Created at

2022-09-05 11:55:34 UTC

Updated at

2022-09-05 11:55:34 UTC

NP-MRD ID

NP0213066

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(7s,9r,18r)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid

Description

2-[(7S,9R,18R)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]Icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Based on a literature review very few articles have been published on 2-[(7S,9R,18R)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]Icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052213552D          

 31 35  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
    4.1403   -0.4125    0.0000 C   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
    3.4259    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
    4.8548    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
    1.2825   -0.4125    0.0000 C   0  0  0  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  0  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  0  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 10 16  1  0  0  0  0
  2 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 23 31  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -3.4049    1.8086   -1.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517    0.6240   -1.0341 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3323    0.8743    0.0051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6897   -0.2416    0.7242 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8016   -1.0014    0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0105   -0.1907   -0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0581    0.9818    0.2605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1141   -0.7526   -0.7617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5824   -1.1967    1.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2496   -0.7241    0.5713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420   -1.2090    1.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0998   -0.7383    0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    0.1827   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656    0.6670   -0.9106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9774    1.5495   -1.9080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833    0.1903   -0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987    0.6490   -0.7202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6428    1.4773   -1.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587    0.1336   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6055   -0.7421    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3194   -1.2245    1.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2582   -2.0731    2.3365 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9116   -1.1634    1.4927 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5728    0.1278    1.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6430    1.1220    0.8775 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8803    2.2443    1.2687 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0602    0.5356   -0.4159 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1452    1.3794   -1.4691 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8027   -0.7777   -0.6278 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2346   -0.4625   -1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462   -1.6057    0.4521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0459    1.5697   -2.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851    2.1015   -2.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9510    2.7103   -1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8678   -0.2275   -1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1111    0.1108    1.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0717   -1.8778    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4582   -1.4454   -0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0611   -0.6525   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7467   -2.1822    0.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -1.4144    2.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1396   -1.9250    2.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2683    2.0047   -2.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8479   -1.9286    2.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9185    0.4717    2.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5578   -0.1696    2.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7084    1.3899    0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0469    2.3394    2.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3088    0.9523   -2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3364   -1.2820   -1.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8929   -0.3255   -0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1887    0.4439   -1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6156   -1.3132   -1.6403 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
 13 14  1  0
 14 15  1  0
 14 16  2  0
 13 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  6
 27 29  1  0
 29 30  1  0
 29 31  1  0
 20 21  1  0
 21 22  2  0
 16  2  1  0
 27 19  1  0
 16 10  1  0
 31 23  1  0
 21 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  6
  4 36  1  1
  5 37  1  0
  5 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 11 42  1  0
 15 43  1  0
 23 44  1  1
 24 45  1  0
 24 46  1  0
 25 47  1  6
 26 48  1  0
 28 49  1  0
 29 50  1  6
 30 51  1  0
 30 52  1  0
 30 53  1  0
M  END


  Mrv1652309052213552D          

 31 35  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
    4.1403   -0.4125    0.0000 C   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
    3.4259    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
    4.8548    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
    1.2825   -0.4125    0.0000 C   0  0  0  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  0  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  0  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 10 16  1  0  0  0  0
  2 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 23 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213066

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](CC(O)=O)CC2=CC3=C(C(O)=C12)C(=O)C1=C(C2CC(O)C1(O)[C@@H](C)O2)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O9/c1-7-15-9(3-10(30-7)5-14(24)25)4-11-16(20(15)27)21(28)18-17(19(11)26)12-6-13(23)22(18,29)8(2)31-12/h4,7-8,10,12-13,23,27,29H,3,5-6H2,1-2H3,(H,24,25)/t7-,8+,10+,12?,13?,22?/m0/s1

> <INCHI_KEY>
QJOFRWDMXPKWGM-PFRINGPSSA-N

> <FORMULA>
C22H22O9

> <MOLECULAR_WEIGHT>
430.409

> <EXACT_MASS>
430.126382288

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
42.632146488926125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.36689396866666624

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.705001866858022

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.399444206682811

> <JCHEM_PKA_STRONGEST_BASIC>
-3.349143681247763

> <JCHEM_POLAR_SURFACE_AREA>
150.59

> <JCHEM_REFRACTIVITY>
105.46729999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-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       7.729  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.395  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.395   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.729   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.729   3.850   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.062   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.061   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.061   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.728   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.728   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.061  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.061  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.394  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.060  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.060   1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.273   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.394   2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.394   3.850   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.137   1.283   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.625   0.990   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.137   0.257   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
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   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10    2                                                  
CONECT   17   13   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   27                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   12   22                                                  
CONECT   22   21                                                            
CONECT   23   20   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   19   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   23                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
2-[(7S,9R,18R)-1,5,19-Trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0,.0,.0,]icosa-2(15),4(13),5,11-tetraen-9-yl]acetate	Generator

Chemical Formula

C₂₂H₂₂O₉

Average Mass

430.4090 Da

Monoisotopic Mass

430.12638 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](CC(O)=O)CC2=CC3=C(C(O)=C12)C(=O)C1=C(C2CC(O)C1(O)[C@@H](C)O2)C3=O

InChI Identifier

InChI=1S/C22H22O9/c1-7-15-9(3-10(30-7)5-14(24)25)4-11-16(20(15)27)21(28)18-17(19(11)26)12-6-13(23)22(18,29)8(2)31-12/h4,7-8,10,12-13,23,27,29H,3,5-6H2,1-2H3,(H,24,25)/t7-,8+,10+,12?,13?,22?/m0/s1

InChI Key

QJOFRWDMXPKWGM-PFRINGPSSA-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 hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Isochromanequinone
Hydroxyanthraquinone
Benzoisochromanequinone
Naphthopyranone
Naphthopyran
2-benzopyran
Naphthalene
Isochromane
Benzopyran
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Pyran
Oxane
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
1,2-diol
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.37	ChemAxon
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	105.47 m³·mol⁻¹	ChemAxon
Polarizability	42.63 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

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

163061425

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(7s,9r,18r)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid (NP0213066)

MOL for NP0213066 ([(7s,9r,18r)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid)

3D MOL for NP0213066 ([(7s,9r,18r)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid)

3D SDF for NP0213066 ([(7s,9r,18r)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid)

3D-SDF for NP0213066 ([(7s,9r,18r)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid)

PDB for NP0213066 ([(7s,9r,18r)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid)

3D PDB for NP0213066 ([(7s,9r,18r)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid)

SMILES for NP0213066 ([(7s,9r,18r)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid)

INCHI for NP0213066 ([(7s,9r,18r)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid)

Structure for NP0213066 ([(7s,9r,18r)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid)

3D Structure for NP0213066 ([(7s,9r,18r)-1,5,19-trihydroxy-7,18-dimethyl-3,14-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),4(13),5,11-tetraen-9-yl]acetic acid)