NP-MRD: Showing NP-Card for Squalestatin H6 (NP0022690)

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Record Information

Version

2.0

Created at

2021-01-06 07:52:43 UTC

Updated at

2021-07-15 17:39:43 UTC

NP-MRD ID

NP0022690

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Squalestatin H6

Provided By

NPAtlas

Description

Squalestatin H6 is found in Phoma sp. C2932. Based on a literature review very few articles have been published on (1S,3S,4S,5R,6R,7R)-4,6,7-trihydroxy-1-[(3Z)-4-hydroxy-3-(2-methyl-3-phenylpropylidene)butyl]-2,8-dioxabicyclo[3.2.1]Octane-3,4,5-tricarboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105373D          

 63 65  0  0  0  0            999 V2000
    4.4624   -1.5499   -1.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497   -0.4745   -0.3928 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3005   -0.6632   -0.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287   -0.8405    0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2792    0.1811    2.5838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0280   -1.0557    0.1719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8402    0.0118    0.7861 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3240   -0.1134    0.4716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4967   -0.0479   -0.8936 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8525   -0.6618   -1.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2533   -2.0787    0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
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  9 10  1  0  0  0  0
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M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242105373D          

 63 65  0  0  0  0            999 V2000
    4.4624   -1.5499   -1.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6797    1.7958   -1.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7959   -0.3422   -0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233    0.6757    0.9757 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1154    1.5073    1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5431    2.3060    2.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4882    1.4159    1.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484    0.9357    1.1455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3854   -0.7984    1.3372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6685   -0.8612    2.7093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9614   -1.3121    1.0844 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9796   -2.4234    0.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1992    0.8553   -0.9812 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6729    0.9155   -0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2298    1.4510    0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5843    1.5346    0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4248    1.0803   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9276    0.5529   -1.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5679    0.4779   -1.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2941   -1.3819   -2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032   -2.5149   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -1.5793   -0.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1733   -0.5242    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8525   -0.6618   -1.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854   -0.8660    2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5398   -1.7895    2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851    1.0521    2.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533   -2.0787    0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894   -1.0462   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5043    0.9969    0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8193   -0.0542    1.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3005   -1.0627   -1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8448   -0.4913   -3.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4177    2.8747   -0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5603   -0.3774    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0101    1.6142    2.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1227   -1.3509    0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8701   -0.6724    3.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4812   -1.5109    2.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3720   -2.3753   -0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513    0.8167   -2.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7247    1.7002   -0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5482    1.7987    1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9816    1.9464    1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5043    1.1607   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5774    0.1951   -2.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534    0.0581   -2.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 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
 11 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 24  9  1  0  0  0  0
 35 30  1  0  0  0  0
 27  9  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  2 39  1  1  0  0  0
  3 40  1  0  0  0  0
  5 41  1  0  0  0  0
  5 42  1  0  0  0  0
  6 43  1  0  0  0  0
  7 44  1  0  0  0  0
  7 45  1  0  0  0  0
  8 46  1  0  0  0  0
  8 47  1  0  0  0  0
 11 48  1  6  0  0  0
 14 49  1  0  0  0  0
 16 50  1  0  0  0  0
 19 51  1  0  0  0  0
 23 52  1  0  0  0  0
 25 53  1  6  0  0  0
 26 54  1  0  0  0  0
 27 55  1  1  0  0  0
 28 56  1  0  0  0  0
 29 57  1  0  0  0  0
 29 58  1  0  0  0  0
 31 59  1  0  0  0  0
 32 60  1  0  0  0  0
 33 61  1  0  0  0  0
 34 62  1  0  0  0  0
 35 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022690

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1([H])O[C@]2(O[C@](C(=O)O[H])([C@]([H])(O[H])[C@@]2([H])O[H])[C@]1(O[H])C(=O)O[H])C([H])([H])C([H])([H])C(=C(/[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H])\C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O12/c1-12(9-13-5-3-2-4-6-13)10-14(11-24)7-8-21-15(25)16(26)23(35-21,20(31)32)22(33,19(29)30)17(34-21)18(27)28/h2-6,10,12,15-17,24-26,33H,7-9,11H2,1H3,(H,27,28)(H,29,30)(H,31,32)/b14-10-/t12-,15+,16+,17+,21-,22+,23-/m0/s1

> <INCHI_KEY>
NNOAULQCFAVIGM-PFGYURHTSA-N

> <FORMULA>
C23H28O12

> <MOLECULAR_WEIGHT>
496.465

> <EXACT_MASS>
496.158076342

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.987106572175584

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,4S,5R,6R,7R)-4,6,7-trihydroxy-1-[(3Z)-4-hydroxy-3-[(2S)-2-methyl-3-phenylpropylidene]butyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.4606355709999995

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.239864794191227

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.373877976981469

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9757420532312882

> <JCHEM_POLAR_SURFACE_AREA>
211.27999999999997

> <JCHEM_REFRACTIVITY>
114.8045

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,4S,5R,6R,7R)-4,6,7-trihydroxy-1-[(3Z)-4-hydroxy-3-[(2S)-2-methyl-3-phenylpropylidene]butyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
    4.4624   -1.5499   -1.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497   -0.4745   -0.3928 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3005   -0.6632   -0.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287   -0.8405    0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015   -0.8619    1.8777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792    0.1811    2.5838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0280   -1.0557    0.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8402    0.0118    0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3240   -0.1134    0.4716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4967   -0.0479   -0.8936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160   -0.0758   -1.2860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9251    0.2471   -2.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9281    0.5052   -3.4257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1764    0.2729   -3.3045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6237    0.9253   -0.4785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1668    2.1886   -0.7959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0682    0.8067   -0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6797    1.7958   -1.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7959   -0.3422   -0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233    0.6757    0.9757 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1154    1.5073    1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5431    2.3060    2.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4882    1.4159    1.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484    0.9357    1.1455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3854   -0.7984    1.3372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6685   -0.8612    2.7093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9614   -1.3121    1.0844 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9796   -2.4234    0.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1992    0.8553   -0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6729    0.9155   -0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2298    1.4510    0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5843    1.5346    0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4248    1.0803   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9276    0.5529   -1.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5679    0.4779   -1.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2941   -1.3819   -2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032   -2.5149   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -1.5793   -0.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1733   -0.5242    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8525   -0.6618   -1.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854   -0.8660    2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5398   -1.7895    2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851    1.0521    2.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533   -2.0787    0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894   -1.0462   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5043    0.9969    0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8193   -0.0542    1.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3005   -1.0627   -1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8448   -0.4913   -3.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4177    2.8747   -0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5603   -0.3774    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0101    1.6142    2.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1227   -1.3509    0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8701   -0.6724    3.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4812   -1.5109    2.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3720   -2.3753   -0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513    0.8167   -2.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7247    1.7002   -0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5482    1.7987    1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9816    1.9464    1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5043    1.1607   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5774    0.1951   -2.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534    0.0581   -2.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  1  0
  9  8  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  1  0
 20 21  1  1
 21 22  2  0
 21 23  1  0
 20 24  1  0
 20 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
  2 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 24  9  1  0
 35 30  1  0
 27  9  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  1
  3 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
 11 48  1  6
 14 49  1  0
 16 50  1  0
 19 51  1  0
 23 52  1  0
 25 53  1  6
 26 54  1  0
 27 55  1  1
 28 56  1  0
 29 57  1  0
 29 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.462  -1.550  -1.219  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.750  -0.475  -0.393  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.301  -0.663  -0.495  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.429  -0.841   0.492  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.902  -0.862   1.878  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.279   0.181   2.584  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.028  -1.056   0.172  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.840   0.012   0.786  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.324  -0.113   0.472  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.497  -0.048  -0.894  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.816  -0.076  -1.286  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.925   0.247  -2.709  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.928   0.505  -3.426  0.00  0.00           O+0
HETATM   14  O   UNK     0      -5.176   0.273  -3.305  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.624   0.925  -0.479  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.167   2.189  -0.796  0.00  0.00           O+0
HETATM   17  C   UNK     0      -6.068   0.807  -0.783  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.680   1.796  -1.263  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.796  -0.342  -0.569  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.323   0.676   0.976  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.115   1.507   1.881  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.543   2.306   2.656  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.488   1.416   1.883  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.948   0.936   1.145  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.385  -0.798   1.337  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.668  -0.861   2.709  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.961  -1.312   1.084  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.980  -2.423   0.252  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.199   0.855  -0.981  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.673   0.916  -0.836  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.230   1.451   0.332  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.584   1.535   0.516  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.425   1.080  -0.473  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.928   0.553  -1.622  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.568   0.478  -1.788  0.00  0.00           C+0
HETATM   36  H   UNK     0       4.294  -1.382  -2.280  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.003  -2.515  -0.877  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.525  -1.579  -0.949  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.173  -0.524   0.599  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.853  -0.662  -1.504  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.985  -0.866   2.033  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.540  -1.790   2.422  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.485   1.052   2.143  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.253  -2.079   0.586  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.189  -1.046  -0.924  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.504   0.997   0.487  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.819  -0.054   1.919  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.301  -1.063  -1.123  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.845  -0.491  -3.230  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.418   2.875  -0.121  0.00  0.00           H+0
HETATM   51  H   UNK     0      -7.560  -0.377   0.092  0.00  0.00           H+0
HETATM   52  H   UNK     0      -7.010   1.614   2.743  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.123  -1.351   0.753  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.870  -0.672   3.256  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.481  -1.511   2.063  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.372  -2.375  -0.504  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.951   0.817  -2.065  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.725   1.700  -0.455  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.548   1.799   1.088  0.00  0.00           H+0
HETATM   60  H   UNK     0       7.982   1.946   1.413  0.00  0.00           H+0
HETATM   61  H   UNK     0       9.504   1.161  -0.296  0.00  0.00           H+0
HETATM   62  H   UNK     0       8.577   0.195  -2.401  0.00  0.00           H+0
HETATM   63  H   UNK     0       6.153   0.058  -2.706  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    1    3   29   39                                             
CONECT    3    2    4   40                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   41   42                                             
CONECT    6    5   43                                                       
CONECT    7    4    8   44   45                                             
CONECT    8    7    9   46   47                                             
CONECT    9    8   10   24   27                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   15   48                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   49                                                       
CONECT   15   11   16   17   20                                             
CONECT   16   15   50                                                       
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   51                                                       
CONECT   20   15   21   24   25                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   52                                                       
CONECT   24   20    9                                                       
CONECT   25   20   26   27   53                                             
CONECT   26   25   54                                                       
CONECT   27   25   28    9   55                                             
CONECT   28   27   56                                                       
CONECT   29    2   30   57   58                                             
CONECT   30   29   31   35                                                  
CONECT   31   30   32   59                                                  
CONECT   32   31   33   60                                                  
CONECT   33   32   34   61                                                  
CONECT   34   33   35   62                                                  
CONECT   35   34   30   63                                                  
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    2                                                            
CONECT   40    3                                                            
CONECT   41    5                                                            
CONECT   42    5                                                            
CONECT   43    6                                                            
CONECT   44    7                                                            
CONECT   45    7                                                            
CONECT   46    8                                                            
CONECT   47    8                                                            
CONECT   48   11                                                            
CONECT   49   14                                                            
CONECT   50   16                                                            
CONECT   51   19                                                            
CONECT   52   23                                                            
CONECT   53   25                                                            
CONECT   54   26                                                            
CONECT   55   27                                                            
CONECT   56   28                                                            
CONECT   57   29                                                            
CONECT   58   29                                                            
CONECT   59   31                                                            
CONECT   60   32                                                            
CONECT   61   33                                                            
CONECT   62   34                                                            
CONECT   63   35                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  130    0
END

RDKit          3D

63 65  0  0  0  0  0  0  0  0999 V2000
    4.4624   -1.5499   -1.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497   -0.4745   -0.3928 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3005   -0.6632   -0.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287   -0.8405    0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015   -0.8619    1.8777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792    0.1811    2.5838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0280   -1.0557    0.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8402    0.0118    0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3240   -0.1134    0.4716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4967   -0.0479   -0.8936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8160   -0.0758   -1.2860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9251    0.2471   -2.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9281    0.5052   -3.4257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1764    0.2729   -3.3045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6237    0.9253   -0.4785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1668    2.1886   -0.7959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0682    0.8067   -0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6797    1.7958   -1.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7959   -0.3422   -0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233    0.6757    0.9757 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1154    1.5073    1.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5431    2.3060    2.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4882    1.4159    1.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484    0.9357    1.1455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3854   -0.7984    1.3372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6685   -0.8612    2.7093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9614   -1.3121    1.0844 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9796   -2.4234    0.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1992    0.8553   -0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6729    0.9155   -0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2298    1.4510    0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5843    1.5346    0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4248    1.0803   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9276    0.5529   -1.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5679    0.4779   -1.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2941   -1.3819   -2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032   -2.5149   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -1.5793   -0.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1733   -0.5242    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8525   -0.6618   -1.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854   -0.8660    2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5398   -1.7895    2.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4851    1.0521    2.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533   -2.0787    0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894   -1.0462   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5043    0.9969    0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8193   -0.0542    1.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3005   -1.0627   -1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8448   -0.4913   -3.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4177    2.8747   -0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5603   -0.3774    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0101    1.6142    2.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1227   -1.3509    0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8701   -0.6724    3.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4812   -1.5109    2.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3720   -2.3753   -0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513    0.8167   -2.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7247    1.7002   -0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5482    1.7987    1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9816    1.9464    1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5043    1.1607   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5774    0.1951   -2.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534    0.0581   -2.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  1  0
  9  8  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  1  0
 20 21  1  1
 21 22  2  0
 21 23  1  0
 20 24  1  0
 20 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
  2 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 24  9  1  0
 35 30  1  0
 27  9  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  1
  3 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  0
  8 47  1  0
 11 48  1  6
 14 49  1  0
 16 50  1  0
 19 51  1  0
 23 52  1  0
 25 53  1  6
 26 54  1  0
 27 55  1  1
 28 56  1  0
 29 57  1  0
 29 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(1S,3S,4S,5R,6R,7R)-4,6,7-Trihydroxy-1-[(3Z)-4-hydroxy-3-(2-methyl-3-phenylpropylidene)butyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate	Generator

Chemical Formula

C₂₃H₂₈O₁₂

Average Mass

496.4650 Da

Monoisotopic Mass

496.15808 Da

IUPAC Name

(1S,3S,4S,5R,6R,7R)-4,6,7-trihydroxy-1-[(3Z)-4-hydroxy-3-[(2S)-2-methyl-3-phenylpropylidene]butyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

Traditional Name

(1S,3S,4S,5R,6R,7R)-4,6,7-trihydroxy-1-[(3Z)-4-hydroxy-3-[(2S)-2-methyl-3-phenylpropylidene]butyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

CAS Registry Number

Not Available

SMILES

CC(CC1=CC=CC=C1)\C=C(/CO)CC[C@]12O[C@@]([C@H](O)[C@H]1O)(C(O)=O)[C@@](O)([C@H](O2)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C23H28O12/c1-12(9-13-5-3-2-4-6-13)10-14(11-24)7-8-21-15(25)16(26)23(35-21,20(31)32)22(33,19(29)30)17(34-21)18(27)28/h2-6,10,12,15-17,24-26,33H,7-9,11H2,1H3,(H,27,28)(H,29,30)(H,31,32)/b14-10-/t12?,15-,16-,17-,21+,22-,23+/m1/s1

InChI Key

NNOAULQCFAVIGM-PFGYURHTSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Phoma sp. C2932	NPAtlas	8071119

Chemical Taxonomy

Classification

Not classified

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	0.44	ALOGPS
logP	0.46	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	211.28 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	114.8 m³·mol⁻¹	ChemAxon
Polarizability	47.99 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA015326

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78439794

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587366

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Squalestatin H6 (NP0022690)

MOL for NP0022690 (Squalestatin H6)

3D MOL for NP0022690 (Squalestatin H6)

3D SDF for NP0022690 (Squalestatin H6)

3D-SDF for NP0022690 (Squalestatin H6)

PDB for NP0022690 (Squalestatin H6)

3D PDB for NP0022690 (Squalestatin H6)

SMILES for NP0022690 (Squalestatin H6)

INCHI for NP0022690 (Squalestatin H6)

Structure for NP0022690 (Squalestatin H6)

3D Structure for NP0022690 (Squalestatin H6)