NP-MRD: Showing NP-Card for (1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione (NP0291629)

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Record Information

Version

1.0

Created at

2022-09-09 22:47:34 UTC

Updated at

2022-09-09 22:47:35 UTC

NP-MRD ID

NP0291629

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione

Description

CHEMBL3334761 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. (1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione is found in Streptomyces violaceoruber. Based on a literature review very few articles have been published on CHEMBL3334761.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200472D          

 32 37  0  0  1  0            999 V2000
    5.1251    2.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2970    2.1719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0818    1.9173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2537    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9684    0.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7972   -0.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3495   -0.7216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768   -0.1954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6409    0.5581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8561    0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2433    0.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4152   -0.5466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4585    0.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2866    1.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995    1.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7275    2.6810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6842    1.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5019    1.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3300    2.3832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8890    1.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0610    0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -0.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0176   -0.8443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481   -0.3352    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6634   -0.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4915    0.7262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2933    0.9808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043    1.2786    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9324    2.0855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0844    0.7120    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3251    0.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1990    0.1741    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
  9  8  1  1  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
 11 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
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
  2 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 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
 20 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

 52 57  0  0  0  0  0  0  0  0999 V2000
    3.2734    3.2119   -0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5735    1.8151    0.1187 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7481    1.3916   -0.4291 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0782    0.0836   -0.1419 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3055   -0.1888    1.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1276   -1.6753    1.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5904   -2.4954    2.1895 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3203   -2.0295    0.2927 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0622   -0.9139   -0.5535 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6760   -0.4100   -0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5869   -1.2642   -0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8310   -2.5800   -0.9116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764   -0.8488   -0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0626    0.4961   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1195    1.3587    0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9867    2.6676    0.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    0.8949   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    0.9458    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6231    2.1105    0.3110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3800   -0.0227   -0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663   -1.2934   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8318   -1.7827   -0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6118   -2.9803   -0.9533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3987   -2.1129   -0.6806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2006   -2.0095    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3476   -0.5789    1.0592 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6190   -0.3329    2.2277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8462    0.3106   -0.0751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0523    1.6382    0.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5039   -0.1883   -1.3299 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3127    0.8014   -2.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1268   -1.4576   -1.6902 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9638    3.9021    0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5633    3.2040   -1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2156    3.6431   -0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549    1.9495    1.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0280   -0.1408   -0.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5485    0.2335    1.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3475    0.0811    1.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1714   -1.2250   -1.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7019   -3.0300   -1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1776    3.1751    0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1892   -3.1464   -0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1950   -2.4995    0.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6065   -2.5453    1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4280   -0.3728    1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2636   -0.4658    2.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9932    1.8124    1.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6185   -0.2219   -1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0561    1.6085   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3055    1.2381   -2.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5378    0.2389   -3.4077 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  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 14 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 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
 21 22  1  0
 22 23  2  0
 17  2  1  0
 28 20  1  0
  9  4  1  0
 17 10  1  0
 32 24  1  0
 22 13  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  1
  4 37  1  6
  5 38  1  0
  5 39  1  0
  9 40  1  6
 12 41  1  0
 16 42  1  0
 24 43  1  6
 25 44  1  0
 25 45  1  0
 26 46  1  1
 27 47  1  0
 29 48  1  0
 30 49  1  1
 31 50  1  0
 31 51  1  0
 31 52  1  0
M  END


  Mrv1652309102200472D          

 32 37  0  0  1  0            999 V2000
    5.1251    2.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2970    2.1719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0818    1.9173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2537    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9684    0.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7972   -0.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3495   -0.7216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768   -0.1954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6409    0.5581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8561    0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2433    0.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4152   -0.5466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4585    0.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2866    1.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995    1.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7275    2.6810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6842    1.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5019    1.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3300    2.3832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8890    1.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0610    0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -0.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0176   -0.8443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481   -0.3352    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6634   -0.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4915    0.7262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2933    0.9808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043    1.2786    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9324    2.0855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0844    0.7120    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3251    0.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1990    0.1741    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
  9  8  1  1  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
 11 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
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
  2 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 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
 20 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>
NP0291629

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@H]2CC(=O)O[C@H]2C2=C(O)C3=C(C(O)=C12)C(=O)C1=C([C@H]2C[C@@H](O)[C@]1(O)[C@@H](C)O2)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O10/c1-5-11-15(21-8(30-5)4-10(24)32-21)19(27)13-14(17(11)25)20(28)16-12(18(13)26)7-3-9(23)22(16,29)6(2)31-7/h5-9,21,23,25,27,29H,3-4H2,1-2H3/t5-,6+,7+,8-,9+,21+,22+/m0/s1

> <INCHI_KEY>
ONQCWTVJMHJRFM-LHKCJDRRSA-N

> <FORMULA>
C22H20O10

> <MOLECULAR_WEIGHT>
444.392

> <EXACT_MASS>
444.105646844

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.5670690902804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,7S,11S,13S,19S,20R,23R)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0^{2,18}.0^{4,16}.0^{6,14}.0^{7,11}]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione

> <JCHEM_LOGP>
0.4588036246666659

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.639191409254687

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.855805067217507

> <JCHEM_PKA_STRONGEST_BASIC>
-3.349143700187958

> <JCHEM_POLAR_SURFACE_AREA>
159.81999999999996

> <JCHEM_REFRACTIVITY>
105.1635

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,7S,11S,13S,19S,20R,23R)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0^{2,18}.0^{4,16}.0^{6,14}.0^{7,11}]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       9.567   5.560   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.888   4.054   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.353   3.579   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.674   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.008   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.688  -0.203   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.719  -1.347   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      11.157  -0.365   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.530   1.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.065   1.517   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.921   0.486   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.242  -1.020   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.456   0.961   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.135   2.467   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.279   3.498   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.958   5.005   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.744   3.023   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.670   2.942   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.349   4.449   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.526   1.911   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.847   0.405   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.312  -0.070   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.633  -1.576   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.703  -0.626   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.238  -0.151   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.917   1.356   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.547   1.831   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.061   2.387   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.740   3.893   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.024   1.329   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.607   0.727   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.238   0.325   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   22                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10    2                                                  
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   28                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   13   23                                                  
CONECT   23   22                                                            
CONECT   24   21   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   20   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   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀O₁₀

Average Mass

444.3920 Da

Monoisotopic Mass

444.10565 Da

IUPAC Name

(1R,7S,11S,13S,19S,20R,23R)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0^{2,18}.0^{4,16}.0^{6,14}.0^{7,11}]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione

Traditional Name

(1R,7S,11S,13S,19S,20R,23R)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0^{2,18}.0^{4,16}.0^{6,14}.0^{7,11}]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@H]2CC(=O)O[C@H]2C2=C(O)C3=C(C(O)=C12)C(=O)C1=C([C@H]2C[C@@H](O)[C@]1(O)[C@@H](C)O2)C3=O

InChI Identifier

InChI=1S/C22H20O10/c1-5-11-15(21-8(30-5)4-10(24)32-21)19(27)13-14(17(11)25)20(28)16-12(18(13)26)7-3-9(23)22(16,29)6(2)31-7/h5-9,21,23,25,27,29H,3-4H2,1-2H3/t5-,6+,7+,8-,9+,21+,22+/m0/s1

InChI Key

ONQCWTVJMHJRFM-LHKCJDRRSA-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 violaceoruber	LOTUS Database	35616633

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

Benzoisochromanequinone
Hydroxyanthraquinone
Isochromanequinone
Naphthopyranone
Naphthopyran
Benzopyran
Isochromane
2-benzopyran
Naphthalene
Aryl ketone
Quinone
Phenol
Pyranone
Gamma butyrolactone
Oxane
Pyran
Tertiary alcohol
Oxolane
Vinylogous acid
1,2-diol
Carboxylic acid ester
Secondary alcohol
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen 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	0.46	ChemAxon
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	159.82 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	105.16 m³·mol⁻¹	ChemAxon
Polarizability	42.57 Å³	ChemAxon
Number of Rings	6	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

49787012

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione (NP0291629)

MOL for NP0291629 ((1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione)

3D MOL for NP0291629 ((1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione)

3D SDF for NP0291629 ((1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione)

3D-SDF for NP0291629 ((1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione)

PDB for NP0291629 ((1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione)

3D PDB for NP0291629 ((1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione)

SMILES for NP0291629 ((1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione)

INCHI for NP0291629 ((1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione)

Structure for NP0291629 ((1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione)

3D Structure for NP0291629 ((1r,7s,11s,13s,19s,20r,23r)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0²,¹⁸.0⁴,¹⁶.0⁶,¹⁴.0⁷,¹¹]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione)