NP-MRD: Showing NP-Card for Bendigole F (NP0010139)

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Record Information

Version

2.0

Created at

2021-01-05 19:45:38 UTC

Updated at

2021-07-15 17:05:15 UTC

NP-MRD ID

NP0010139

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bendigole F

Provided By

NPAtlas

Description

Bendigole f belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Thus, bendigole F is considered to be a bile acid. Bendigole F is found in Actinomadura sp. SBMs009. Based on a literature review very few articles have been published on Bendigole f.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106553D          

 63 66  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242106553D          

 63 66  0  0  0  0            999 V2000
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   -3.3074    0.5180    1.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6866    2.2433    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7267    2.6884   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5932    1.7664   -1.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5872    2.1418   -1.7952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2304    0.3518   -1.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2011   -0.0712   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8724   -1.5507   -0.3446 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4159   -1.7487   -0.7141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3110   -1.6160   -2.1112 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9848    0.7105    2.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309    1.6517    1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6937    0.3907    2.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4238   -1.4041    1.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2439   -1.3621   -0.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4502   -0.8967    0.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8853    1.0300   -1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9977    1.4838   -0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    0.2676   -4.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1200    0.4696   -0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6570   -2.4586   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2763   -1.4383   -1.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163   -2.5432   -1.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4793   -2.9654   -0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1055   -0.1524   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721   -0.9995    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1048    0.6248   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3021    1.8611   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2316    2.4543    0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1384    1.0356    2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8318    2.8851    1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600   -2.0840    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060   -1.7430    2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1814   -0.7035    2.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5002    1.0769    2.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3896   -0.5451    2.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2672    0.9861    2.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0777    3.0305    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9324    3.7790   -0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8544   -0.3929   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5034   -2.0876   -1.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0750   -1.9149    0.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1576   -2.8032   -0.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8626   -2.3243   -2.5549 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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  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  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 13 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17  8  1  0  0  0  0
 26 19  1  0  0  0  0
 17 11  1  0  0  0  0
 28 12  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  2 33  1  1  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
  7 38  1  0  0  0  0
  8 39  1  6  0  0  0
  9 40  1  0  0  0  0
  9 41  1  0  0  0  0
 10 42  1  0  0  0  0
 10 43  1  0  0  0  0
 11 44  1  6  0  0  0
 12 45  1  1  0  0  0
 13 46  1  6  0  0  0
 14 47  1  0  0  0  0
 14 48  1  0  0  0  0
 15 49  1  1  0  0  0
 16 50  1  0  0  0  0
 18 51  1  0  0  0  0
 18 52  1  0  0  0  0
 18 53  1  0  0  0  0
 20 54  1  0  0  0  0
 20 55  1  0  0  0  0
 20 56  1  0  0  0  0
 21 57  1  0  0  0  0
 22 58  1  0  0  0  0
 25 59  1  0  0  0  0
 27 60  1  0  0  0  0
 27 61  1  0  0  0  0
 28 62  1  6  0  0  0
 29 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010139

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]1([H])C([H])([H])C([H])([H])[C@@]2([H])[C@]3([H])[C@]([H])(O[H])C([H])([H])C4=C([H])C(=O)C([H])=C([H])[C@]4(C([H])([H])[H])[C@@]3([H])C([H])([H])[C@]([H])(O[H])[C@]12C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h8-10,13,16-20,22,26-27H,4-7,11-12H2,1-3H3,(H,28,29)/t13-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

> <INCHI_KEY>
QKYFOPPSEWXMGR-DFQOQHGMSA-N

> <FORMULA>
C24H34O5

> <MOLECULAR_WEIGHT>
402.531

> <EXACT_MASS>
402.240624195

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.352861024283655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]pentanoic acid

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
2.6419844130000003

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.87089157975592

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.475012521063312

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15750472182510877

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
111.68119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
    3.7140    0.6496    1.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3640   -0.4399    0.7772 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5080   -0.5839   -0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7726    0.6727   -1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8842    0.5027   -1.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829    0.0729   -1.5460 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7215    0.8107   -3.2875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054   -0.3785    0.0502 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0348   -1.6370   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5804   -2.1215   -0.7348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0856   -0.8653   -0.4062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4843   -0.8507    0.0097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9405    0.6008   -0.2477 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8550    1.5173    0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2330    1.0390    1.0065 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1885    2.0861    0.9677 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -0.3047    0.7279 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6531   -1.2528    1.9082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3016    0.8409    0.3481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3074    0.5180    1.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6866    2.2433    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7267    2.6884   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5932    1.7664   -1.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5872    2.1418   -1.7952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2304    0.3518   -1.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2011   -0.0712   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8724   -1.5507   -0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4159   -1.7487   -0.7141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3110   -1.6160   -2.1112 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9848    0.7105    2.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309    1.6517    1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6937    0.3907    2.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4238   -1.4041    1.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2439   -1.3621   -0.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4502   -0.8967    0.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8853    1.0300   -1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9977    1.4838   -0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    0.2676   -4.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1200    0.4696   -0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6570   -2.4586   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2763   -1.4383   -1.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163   -2.5432   -1.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4793   -2.9654   -0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1055   -0.1524   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721   -0.9995    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1048    0.6248   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3021    1.8611   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2316    2.4543    0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1384    1.0356    2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8318    2.8851    1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600   -2.0840    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060   -1.7430    2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1814   -0.7035    2.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5002    1.0769    2.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3896   -0.5451    2.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2672    0.9861    2.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0777    3.0305    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9324    3.7790   -0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8544   -0.3929   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5034   -2.0876   -1.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0750   -1.9149    0.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1576   -2.8032   -0.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8626   -2.3243   -2.5549 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  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  1
 13 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 17  8  1  0
 26 19  1  0
 17 11  1  0
 28 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  1
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  6
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  6
 12 45  1  1
 13 46  1  6
 14 47  1  0
 14 48  1  0
 15 49  1  1
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 22 58  1  0
 25 59  1  0
 27 60  1  0
 27 61  1  0
 28 62  1  6
 29 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       3.714   0.650   1.732  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.364  -0.440   0.777  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.508  -0.584  -0.204  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.773   0.673  -1.010  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.884   0.503  -1.957  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.983   0.073  -1.546  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.721   0.811  -3.288  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.105  -0.379   0.050  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.035  -1.637  -0.834  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.580  -2.122  -0.735  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.086  -0.865  -0.406  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.484  -0.851   0.010  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.940   0.601  -0.248  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.855   1.517   0.084  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.233   1.039   1.006  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.188   2.086   0.968  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.802  -0.305   0.728  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.653  -1.253   1.908  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.302   0.841   0.348  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.307   0.518   1.847  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.687   2.243   0.226  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.727   2.688  -0.450  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.593   1.766  -1.147  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.587   2.142  -1.795  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.230   0.352  -1.046  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.201  -0.071  -0.376  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.872  -1.551  -0.345  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.416  -1.749  -0.714  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.311  -1.616  -2.111  0.00  0.00           O+0
HETATM   30  H   UNK     0       2.985   0.711   2.596  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.831   1.652   1.354  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.694   0.391   2.243  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.424  -1.404   1.371  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.244  -1.362  -0.952  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.450  -0.897   0.285  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.885   1.030  -1.568  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.998   1.484  -0.254  0.00  0.00           H+0
HETATM   38  H   UNK     0       6.099   0.268  -4.063  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.120   0.470  -0.698  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.657  -2.459  -0.412  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.276  -1.438  -1.877  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.316  -2.543  -1.749  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.479  -2.965  -0.043  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.106  -0.152  -1.262  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.672  -1.000   1.097  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.105   0.625  -1.366  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.302   1.861  -0.852  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.232   2.454   0.524  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.138   1.036   2.051  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.832   2.885   1.438  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.060  -2.084   1.696  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.606  -1.743   2.191  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.181  -0.704   2.779  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.500   1.077   2.304  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.390  -0.545   2.063  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.267   0.986   2.217  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.078   3.030   0.744  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.932   3.779  -0.478  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.854  -0.393  -1.559  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.503  -2.088  -1.074  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.075  -1.915   0.659  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.158  -2.803  -0.488  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.863  -2.324  -2.555  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3    8   33                                             
CONECT    3    2    4   34   35                                             
CONECT    4    3    5   36   37                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5   38                                                       
CONECT    8    2    9   17   39                                             
CONECT    9    8   10   40   41                                             
CONECT   10    9   11   42   43                                             
CONECT   11   10   12   17   44                                             
CONECT   12   11   13   28   45                                             
CONECT   13   12   14   19   46                                             
CONECT   14   13   15   47   48                                             
CONECT   15   14   16   17   49                                             
CONECT   16   15   50                                                       
CONECT   17   15   18    8   11                                             
CONECT   18   17   51   52   53                                             
CONECT   19   13   20   21   26                                             
CONECT   20   19   54   55   56                                             
CONECT   21   19   22   57                                                  
CONECT   22   21   23   58                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   59                                                  
CONECT   26   25   27   19                                                  
CONECT   27   26   28   60   61                                             
CONECT   28   27   29   12   62                                             
CONECT   29   28   63                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   14                                                            
CONECT   49   15                                                            
CONECT   50   16                                                            
CONECT   51   18                                                            
CONECT   52   18                                                            
CONECT   53   18                                                            
CONECT   54   20                                                            
CONECT   55   20                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   25                                                            
CONECT   60   27                                                            
CONECT   61   27                                                            
CONECT   62   28                                                            
CONECT   63   29                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  132    0
END

RDKit          3D

63 66  0  0  0  0  0  0  0  0999 V2000
    3.7140    0.6496    1.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3640   -0.4399    0.7772 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5080   -0.5839   -0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7726    0.6727   -1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8842    0.5027   -1.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829    0.0729   -1.5460 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7215    0.8107   -3.2875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054   -0.3785    0.0502 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0348   -1.6370   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5804   -2.1215   -0.7348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0856   -0.8653   -0.4062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4843   -0.8507    0.0097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9405    0.6008   -0.2477 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8550    1.5173    0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2330    1.0390    1.0065 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1885    2.0861    0.9677 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -0.3047    0.7279 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6531   -1.2528    1.9082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3016    0.8409    0.3481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3074    0.5180    1.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6866    2.2433    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7267    2.6884   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5932    1.7664   -1.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5872    2.1418   -1.7952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2304    0.3518   -1.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2011   -0.0712   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8724   -1.5507   -0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4159   -1.7487   -0.7141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3110   -1.6160   -2.1112 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9848    0.7105    2.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309    1.6517    1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6937    0.3907    2.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4238   -1.4041    1.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2439   -1.3621   -0.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4502   -0.8967    0.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8853    1.0300   -1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9977    1.4838   -0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    0.2676   -4.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1200    0.4696   -0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6570   -2.4586   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2763   -1.4383   -1.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163   -2.5432   -1.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4793   -2.9654   -0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1055   -0.1524   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6721   -0.9995    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1048    0.6248   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3021    1.8611   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2316    2.4543    0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1384    1.0356    2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8318    2.8851    1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600   -2.0840    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060   -1.7430    2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1814   -0.7035    2.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5002    1.0769    2.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3896   -0.5451    2.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2672    0.9861    2.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0777    3.0305    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9324    3.7790   -0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8544   -0.3929   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5034   -2.0876   -1.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0750   -1.9149    0.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1576   -2.8032   -0.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8626   -2.3243   -2.5549 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  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  1
 13 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 17  8  1  0
 26 19  1  0
 17 11  1  0
 28 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  1
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  6
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  6
 12 45  1  1
 13 46  1  6
 14 47  1  0
 14 48  1  0
 15 49  1  1
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 22 58  1  0
 25 59  1  0
 27 60  1  0
 27 61  1  0
 28 62  1  6
 29 63  1  0
M  END

View in JSmol View NMR Assignments View DFT Assignments 3D Conformers

Synonyms

Value	Source
7a,12a-Dihydroxy-3-oxochola-1,4-dien-24-Oate	Generator
7a,12a-Dihydroxy-3-oxochola-1,4-dien-24-Oic acid	Generator
7alpha,12alpha-Dihydroxy-3-oxochola-1,4-dien-24-Oate	Generator
7Α,12α-dihydroxy-3-oxochola-1,4-dien-24-Oate	Generator
7Α,12α-dihydroxy-3-oxochola-1,4-dien-24-Oic acid	Generator

Chemical Formula

C₂₄H₃₄O₅

Average Mass

402.5310 Da

Monoisotopic Mass

402.24062 Da

IUPAC Name

(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)CC4=CC(=O)C=C[C@]4(C)[C@H]3C[C@H](O)[C@]12C

InChI Identifier

InChI=1S/C24H34O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h8-10,13,16-20,22,26-27H,4-7,11-12H2,1-3H3,(H,28,29)/t13-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

InChI Key

QKYFOPPSEWXMGR-DFQOQHGMSA-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
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Actinomadura sp. SBMs009	NPAtlas	21684166

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Dihydroxy bile acid, alcohol, or derivatives
3-oxo-delta-1,4-steroid
3-oxosteroid
7-hydroxysteroid
Oxosteroid
12-hydroxysteroid
Hydroxysteroid
Delta-1,4-steroid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010244 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.69	ALOGPS
logP	2.64	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111.68 m³·mol⁻¹	ChemAxon
Polarizability	45.35 Å³	ChemAxon
Number of Rings	4	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

NPAtlas ID

NPA015718

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4447087

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283999

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Bendigole F (NP0010139)

MOL for NP0010139 (Bendigole F)

3D MOL for NP0010139 (Bendigole F)

3D SDF for NP0010139 (Bendigole F)

3D-SDF for NP0010139 (Bendigole F)

PDB for NP0010139 (Bendigole F)

3D PDB for NP0010139 (Bendigole F)

SMILES for NP0010139 (Bendigole F)

INCHI for NP0010139 (Bendigole F)

Structure for NP0010139 (Bendigole F)

3D Structure for NP0010139 (Bendigole F)