NP-MRD: Showing NP-Card for Hemibastadinol 3 (NP0069940)

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Record Information

Version

2.0

Created at

2022-04-28 15:14:17 UTC

Updated at

2022-04-28 15:14:17 UTC

NP-MRD ID

NP0069940

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hemibastadinol 3

Description

Hemibastadinol 3 belongs to the class of organic compounds known as o-bromophenols. These are bromophenols carrying a iodine at the C2 position of the benzene ring. Hemibastadinol 3 is found in Ianthella basta. Based on a literature review very few articles have been published on Hemibastadinol 3.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
   -0.7092   -2.2932    0.9190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618   -1.0869    0.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0818   -0.0948    1.6785 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2806   -0.4354    2.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3149   -0.9482    1.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6099    0.1463    0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5938    1.0777    0.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9053    2.0917   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2485    3.3756    0.3884 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2482    2.1995   -1.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5790    3.2310   -2.1571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2788    1.2953   -1.6646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3612    1.4284   -3.3521 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9803    0.2783   -0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8912   -0.6501    0.2588 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1156    0.7127    0.4318 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0692   -1.3678    0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3224   -0.9568    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0595    0.1127    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2189    0.4740    0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6449   -0.2485   -1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8095    0.1215   -1.6591 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9032   -1.3264   -1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5253   -2.3074   -2.9710 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.7505   -1.6830   -0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7357    0.8896    1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6620    0.4559    2.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1209   -1.2064    3.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2430   -1.2433    1.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9581   -1.8233    0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0788    0.9620    1.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1170    3.3243   -3.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2238   -0.4315   -1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7613   -0.9473   -0.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7640    1.2665   -0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1139   -1.0274    1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9191   -2.4577    0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7470    0.7032    1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7829    1.3272    0.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1302   -0.4003   -2.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1641   -2.5376   -1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
 15  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 25 18  1  0
 14  6  1  0
 16 35  1  0
 15 34  1  6
 17 36  1  0
 17 37  1  0
 19 38  1  0
 20 39  1  0
 22 40  1  0
 25 41  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  7 31  1  0
 11 32  1  0
 14 33  1  0
M  END


  Mrv1652304282217142D          

 25 26  0  0  1  0            999 V2000
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -5.7750    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
 12 22  1  1  0  0  0
  3 23  1  0  0  0  0
  2 24  1  0  0  0  0
  1 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069940

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H](CC1=CC=C(O)C(Br)=C1)C(=O)NCCC1=CC(Br)=C(O)C(Br)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16Br3NO4/c18-11-5-9(1-2-14(11)22)8-15(23)17(25)21-4-3-10-6-12(19)16(24)13(20)7-10/h1-2,5-7,15,22-24H,3-4,8H2,(H,21,25)/t15-/m0/s1

> <INCHI_KEY>
KTCXMUWGHHIRCQ-HNNXBMFYSA-N

> <FORMULA>
C17H16Br3NO4

> <MOLECULAR_WEIGHT>
538.03

> <EXACT_MASS>
534.862947

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
42.721630752628556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-(3-bromo-4-hydroxyphenyl)-N-[2-(3,5-dibromo-4-hydroxyphenyl)ethyl]-2-hydroxypropanamide

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
4.3134918566666665

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.140141630225738

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.738796399846516

> <JCHEM_PKA_STRONGEST_BASIC>
-3.631482710372551

> <JCHEM_POLAR_SURFACE_AREA>
89.79

> <JCHEM_REFRACTIVITY>
106.37550000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-(3-bromo-4-hydroxyphenyl)-N-[2-(3,5-dibromo-4-hydroxyphenyl)ethyl]-2-hydroxypropanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000  -6.160   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -8.470   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   20 Br   UNK     0       9.336  -6.930   0.000  0.00  0.00          Br+0
HETATM   21  O   UNK     0       9.336  -3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23 Br   UNK     0      -8.002  -6.160   0.000  0.00  0.00          Br+0
HETATM   24  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   25 Br   UNK     0      -5.335 -10.780   0.000  0.00  0.00          Br+0
CONECT    1    2    6   25                                                  
CONECT    2    1    3   24                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18                                                            
CONECT   21   17                                                            
CONECT   22   12                                                            
CONECT   23    3                                                            
CONECT   24    2                                                            
CONECT   25    1                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆Br₃NO₄

Average Mass

538.0300 Da

Monoisotopic Mass

534.86295 Da

IUPAC Name

(2S)-3-(3-bromo-4-hydroxyphenyl)-N-[2-(3,5-dibromo-4-hydroxyphenyl)ethyl]-2-hydroxypropanamide

Traditional Name

(2S)-3-(3-bromo-4-hydroxyphenyl)-N-[2-(3,5-dibromo-4-hydroxyphenyl)ethyl]-2-hydroxypropanamide

CAS Registry Number

Not Available

SMILES

O[C@@H](CC1=CC=C(O)C(Br)=C1)C(=O)NCCC1=CC(Br)=C(O)C(Br)=C1

InChI Identifier

InChI=1S/C17H16Br3NO4/c18-11-5-9(1-2-14(11)22)8-15(23)17(25)21-4-3-10-6-12(19)16(24)13(20)7-10/h1-2,5-7,15,22-24H,3-4,8H2,(H,21,25)/t15-/m0/s1

InChI Key

KTCXMUWGHHIRCQ-HNNXBMFYSA-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
Ianthella basta	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-bromophenols. These are bromophenols carrying a iodine at the C2 position of the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

2-bromophenol
1-hydroxy-2-unsubstituted benzenoid
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Fatty acyl
Fatty amide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Alcohol
Organohalogen compound
Organobromide
Organonitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.06	ALOGPS
logP	4.31	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	6.74	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	89.79 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.38 m³·mol⁻¹	ChemAxon
Polarizability	42.72 Å³	ChemAxon
Number of Rings	2	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00028340

Chemspider ID

8567879

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10392437

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Hemibastadinol 3 (NP0069940)

MOL for NP0069940 (Hemibastadinol 3)

3D MOL for NP0069940 (Hemibastadinol 3)

3D SDF for NP0069940 (Hemibastadinol 3)

3D-SDF for NP0069940 (Hemibastadinol 3)

PDB for NP0069940 (Hemibastadinol 3)

3D PDB for NP0069940 (Hemibastadinol 3)

SMILES for NP0069940 (Hemibastadinol 3)

INCHI for NP0069940 (Hemibastadinol 3)

Structure for NP0069940 (Hemibastadinol 3)

3D Structure for NP0069940 (Hemibastadinol 3)