NP-MRD: Showing NP-Card for Hygrocin A (NP0006157)

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Record Information

Version

2.0

Created at

2020-12-09 03:12:30 UTC

Updated at

2024-09-12 20:26:55 UTC

NP-MRD ID

NP0006157

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hygrocin A

Provided By

NPAtlas

Description

Hygrocin A is found in Streptomyces hygroscopicus. Hygrocin A was first documented in 2005 (PMID: 16378365). Based on a literature review a small amount of articles have been published on Hygrocin A (PMID: 24490633) (PMID: 31853567).

Structure

MOL SDF PDB SMILES InChI

NP0006157
  Mrv2104 05272322593D          

 68 70  0  0  0  0            999 V2000
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M  END

NP0006157
  Mrv2104 05272322593D          

 68 70  0  0  0  0            999 V2000
   -1.4420   -3.3078    3.5572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0060   -3.5903    3.1722 C   0  0  1  0  0  0  0  0  0  0  0  0
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 28 63  1  0  0  0  0
 30 64  1  0  0  0  0
 34 65  1  0  0  0  0
 34 66  1  0  0  0  0
 35 67  1  0  0  0  0
 35 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006157

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C3=C(C([H])=C1C([H])([H])[H])C(=O)C(N([H])C(=O)C([H])([H])\C([H])=C(\C(=O)O[C@@]([H])(C([H])([H])[H])[C@@]([H])(O[H])\C([H])=C([H])\[C@@]([H])(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])C2=O)C([H])([H])[H])=C([H])C3=O

> <INCHI_IDENTIFIER>
InChI=1/C28H31NO8/c1-5-17-7-9-20(30)16(4)37-28(36)14(2)6-11-23(33)29-19-13-22(32)24-18(27(19)35)12-15(3)26(34)25(24)21(31)10-8-17/h6-7,9,12-13,16-17,20,30,34H,5,8,10-11H2,1-4H3,(H,29,33)/b9-7+,14-6+/t16-,17+,20-/s2

> <INCHI_KEY>
ZLKHATAJGWAFJX-POUKLUDXNA-N

> <FORMULA>
C28H31NO8

> <MOLECULAR_WEIGHT>
509.555

> <EXACT_MASS>
509.204966962

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.48218647913769

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9S,10E,12S,13S,16E)-9-ethyl-4,12-dihydroxy-3,13,16-trimethyl-14-oxa-20-azatricyclo[19.3.1.0^{5,24}]pentacosa-1(24),2,4,10,16,21-hexaene-6,15,19,23,25-pentone

> <JCHEM_LOGP>
3.489384934333331

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.70141335661361

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.445770643850854

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3160116376596345

> <JCHEM_POLAR_SURFACE_AREA>
147.07

> <JCHEM_REFRACTIVITY>
139.58239999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9S,10E,12S,13S,16E)-9-ethyl-4,12-dihydroxy-3,13,16-trimethyl-14-oxa-20-azatricyclo[19.3.1.0^{5,24}]pentacosa-1(24),2,4,10,16,21-hexaene-6,15,19,23,25-pentone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: NP0006157                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0      -1.442  -3.308   3.557  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.006  -3.590   3.172  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.607  -2.536   2.214  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.124  -2.565   0.888  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.890  -1.560   0.434  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.596  -1.533  -0.893  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.991  -0.463  -1.635  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.127  -1.296  -0.760  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.839  -1.449  -2.104  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.313   0.088  -0.363  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.654   0.308   0.929  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.074  -0.523   1.715  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.230   1.690   1.319  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.874   1.827   2.771  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.124   2.666   0.394  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.479   4.010   0.614  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.834   4.546  -0.660  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.450   5.356  -1.364  0.00  0.00           O+0
HETATM   19  N   UNK     0      -0.598   4.158  -1.086  0.00  0.00           N+0
HETATM   20  C   UNK     0       0.312   3.176  -0.758  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.215   2.250   0.194  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.226   1.195   0.394  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.237   0.619   1.469  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.204   0.934  -0.676  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.413   1.971  -1.595  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.405   1.870  -2.581  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.169   0.709  -2.709  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.184   0.614  -3.814  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.874  -0.369  -1.868  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.525  -1.552  -2.126  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.921  -0.267  -0.826  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.649  -1.538  -0.104  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.404  -2.514  -0.823  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.943  -1.691   1.372  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.125  -2.803   2.049  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.546   3.171  -1.609  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.797   4.137  -2.328  0.00  0.00           O+0
HETATM   38  H   UNK     0      -2.114  -3.364   2.696  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.535  -2.314   4.009  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.783  -4.037   4.298  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.592  -3.613   4.097  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.078  -4.592   2.734  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.489  -1.553   2.687  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.016  -3.453   0.273  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.006  -0.683   1.065  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.413  -2.463  -1.445  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.599   0.293  -1.546  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.568  -1.999  -0.043  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.701  -2.451  -2.514  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.475  -0.721  -2.836  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.912  -1.260  -1.986  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.658   1.409   3.408  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.943   1.292   2.985  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.747   2.869   3.079  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.472   2.486  -0.622  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.258   4.732   0.897  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.736   4.020   1.417  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.318   4.704  -1.905  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.587   2.193   0.908  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.561   2.691  -3.283  0.00  0.00           H+0
HETATM   61  H   UNK     0       5.905  -0.189  -3.643  0.00  0.00           H+0
HETATM   62  H   UNK     0       5.755   1.546  -3.886  0.00  0.00           H+0
HETATM   63  H   UNK     0       4.677   0.435  -4.764  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.923  -2.287  -1.868  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.003  -1.974   1.426  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.872  -0.757   1.927  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.274  -3.751   1.514  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.559  -2.947   3.047  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    1    3   41   42                                             
CONECT    3    2    4   35   43                                             
CONECT    4    3    5   44                                                  
CONECT    5    4    6   45                                                  
CONECT    6    5    7    8   46                                             
CONECT    7    6   47                                                       
CONECT    8    6    9   10   48                                             
CONECT    9    8   49   50   51                                             
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13   52   53   54                                             
CONECT   15   13   16   55                                                  
CONECT   16   15   17   56   57                                             
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   58                                                  
CONECT   20   19   21   36                                                  
CONECT   21   20   22   59                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   31                                                  
CONECT   25   24   26   36                                                  
CONECT   26   25   27   60                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   61   62   63                                             
CONECT   29   27   30   31                                                  
CONECT   30   29   64                                                       
CONECT   31   29   32   24                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   65   66                                             
CONECT   35   34    3   67   68                                             
CONECT   36   25   37   20                                                  
CONECT   37   36                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    2                                                            
CONECT   42    2                                                            
CONECT   43    3                                                            
CONECT   44    4                                                            
CONECT   45    5                                                            
CONECT   46    6                                                            
CONECT   47    7                                                            
CONECT   48    8                                                            
CONECT   49    9                                                            
CONECT   50    9                                                            
CONECT   51    9                                                            
CONECT   52   14                                                            
CONECT   53   14                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   16                                                            
CONECT   58   19                                                            
CONECT   59   21                                                            
CONECT   60   26                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
CONECT   63   28                                                            
CONECT   64   30                                                            
CONECT   65   34                                                            
CONECT   66   34                                                            
CONECT   67   35                                                            
CONECT   68   35                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  140    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₁NO₈

Average Mass

509.5550 Da

Monoisotopic Mass

509.20497 Da

IUPAC Name

(9S,10E,12S,13S,16E)-9-ethyl-4,12-dihydroxy-3,13,16-trimethyl-14-oxa-20-azatricyclo[19.3.1.0^{5,24}]pentacosa-1(24),2,4,10,16,21-hexaene-6,15,19,23,25-pentone

Traditional Name

(9S,10E,12S,13S,16E)-9-ethyl-4,12-dihydroxy-3,13,16-trimethyl-14-oxa-20-azatricyclo[19.3.1.0^{5,24}]pentacosa-1(24),2,4,10,16,21-hexaene-6,15,19,23,25-pentone

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C3=C(C([H])=C1C([H])([H])[H])C(=O)C(N([H])C(=O)C([H])([H])\C([H])=C(\C(=O)O[C@@]([H])(C([H])([H])[H])[C@@]([H])(O[H])\C([H])=C([H])\[C@@]([H])(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])C2=O)C([H])([H])[H])=C([H])C3=O

InChI Identifier

InChI=1/C28H31NO8/c1-5-17-7-9-20(30)16(4)37-28(36)14(2)6-11-23(33)29-19-13-22(32)24-18(27(19)35)12-15(3)26(34)25(24)21(31)10-8-17/h6-7,9,12-13,16-17,20,30,34H,5,8,10-11H2,1-4H3,(H,29,33)/b9-7+,14-6+/t16-,17+,20-/s2

InChI Key

ZLKHATAJGWAFJX-POUKLUDXNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces hygroscopicus	NPAtlas	16378365

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	3.49	ChemAxon
pKa (Strongest Acidic)	7.45	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	147.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	139.58 m³·mol⁻¹	ChemAxon
Polarizability	52.48 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA004945

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cai P, Kong F, Ruppen ME, Glasier G, Carter GT: Hygrocins a and B, naphthoquinone macrolides from Streptomyces hygroscopicus. J Nat Prod. 2005 Dec;68(12):1736-42. doi: 10.1021/np050272l. [PubMed:16378365 ]
Lu C, Li Y, Deng J, Li S, Shen Y, Wang H, Shen Y: Hygrocins C-G, cytotoxic naphthoquinone ansamycins from gdmAI-disrupted Streptomyces sp. LZ35. J Nat Prod. 2013 Dec 27;76(12):2175-9. doi: 10.1021/np400474s. Epub 2013 Nov 18. [PubMed:24490633 ]
Liu Q, Lin Q, Li X, Ali M, He J: Construction and application of a "superplasmid" for enhanced production of antibiotics. Appl Microbiol Biotechnol. 2020 Feb;104(4):1647-1660. doi: 10.1007/s00253-019-10283-6. Epub 2019 Dec 18. [PubMed:31853567 ]

Showing NP-Card for Hygrocin A (NP0006157)

MOL for NP0006157 (Hygrocin A)

3D MOL for NP0006157 (Hygrocin A)

3D SDF for NP0006157 (Hygrocin A)

3D-SDF for NP0006157 (Hygrocin A)

PDB for NP0006157 (Hygrocin A)

3D PDB for NP0006157 (Hygrocin A)

SMILES for NP0006157 (Hygrocin A)

INCHI for NP0006157 (Hygrocin A)

Structure for NP0006157 (Hygrocin A)

3D Structure for NP0006157 (Hygrocin A)