NP-MRD: Showing NP-Card for (+)-Bromophycolide D (NP0077898)

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Record Information

Version

2.0

Created at

2022-04-28 23:02:30 UTC

Updated at

2022-04-28 23:02:30 UTC

NP-MRD ID

NP0077898

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Bromophycolide D

Description

Bromophycolide A belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Bromophycolide A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (+)-Bromophycolide D is found in Callophycus serratus. (+)-Bromophycolide D was first documented in 2011 (PMID: 21732541). Based on a literature review a small amount of articles have been published on bromophycolide A (PMID: 35290044) (PMID: 24159368) (PMID: 22214291) (PMID: 21309525).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201022D          

 34 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292201022D          

 34 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0077898

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2CC3=C(O)C=CC(=C3)C(=O)O[C@@H](CC[C@](C)(O)[C@H](Br)CC[C@]2(C)[C@@H](Br)CC1)C(C)(C)Br

> <INCHI_IDENTIFIER>
InChI=1S/C27H37Br3O4/c1-16-6-9-21(28)26(4)12-10-22(29)27(5,33)13-11-23(25(2,3)30)34-24(32)17-7-8-20(31)18(14-17)15-19(16)26/h7-8,14,21-23,31,33H,6,9-13,15H2,1-5H3/t21-,22+,23-,26-,27-/m0/s1

> <INCHI_KEY>
SKIHYPQTROYIIT-VHXXJFIISA-N

> <FORMULA>
C27H37Br3O4

> <MOLECULAR_WEIGHT>
665.301

> <EXACT_MASS>
662.024199

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
59.510212273817515

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(7S,8S,11R,12S,15S)-7,11-dibromo-15-(2-bromopropan-2-yl)-12,21-dihydroxy-4,8,12-trimethyl-16-oxatricyclo[16.3.1.0^{3,8}]docosa-1(21),3,18(22),19-tetraen-17-one

> <ALOGPS_LOGP>
6.89

> <JCHEM_LOGP>
7.482095389333333

> <ALOGPS_LOGS>
-5.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.048111993450743

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.298565962984167

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2151561522215575

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
148.5936

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.99e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7S,8S,11R,12S,15S)-7,11-dibromo-15-(2-bromopropan-2-yl)-12,21-dihydroxy-4,8,12-trimethyl-16-oxatricyclo[16.3.1.0^{3,8}]docosa-1(21),3,18(22),19-tetraen-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       9.213   2.154   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.183   3.694   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.501   4.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.011   3.741   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.511   4.090   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.307   2.772   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      13.299   1.607   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.862   2.162   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.259  -0.077   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.940  -0.873   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.971  -2.413   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.652  -3.209   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.304  -2.465   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.986  -3.261   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.637  -2.518   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.607  -0.978   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.744   0.446   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.274  -0.926   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.925  -0.182   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.895   1.358   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.746  -1.117   0.000  0.00  0.00           C+0
HETATM   22 Br   UNK     0       6.996   1.046   0.000  0.00  0.00          Br+0
HETATM   23  C   UNK     0       8.016  -4.801   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.319  -3.157   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.638  -2.361   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.607  -0.821   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.349  -4.696   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.109   5.509   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.708   6.928   0.000  0.00  0.00           C+0
HETATM   30 Br   UNK     0      15.528   4.910   0.000  0.00  0.00          Br+0
HETATM   31  C   UNK     0      12.691   6.108   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.643   3.717   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.342   4.983   0.000  0.00  0.00           O+0
HETATM   34 Br   UNK     0      10.562   1.410   0.000  0.00  0.00          Br+0
CONECT    1    2   20   34                                                  
CONECT    2    1    3   32   33                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   13   19   21                                             
CONECT   19   18   20                                                       
CONECT   20   19    1                                                       
CONECT   21   18                                                            
CONECT   22   17                                                            
CONECT   23   14                                                            
CONECT   24   11   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25    9                                                       
CONECT   27   24                                                            
CONECT   28    5   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32    2                                                            
CONECT   33    2                                                            
CONECT   34    1                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₇Br₃O₄

Average Mass

665.3010 Da

Monoisotopic Mass

662.02420 Da

IUPAC Name

(7S,8S,11R,12S,15S)-7,11-dibromo-15-(2-bromopropan-2-yl)-12,21-dihydroxy-4,8,12-trimethyl-16-oxatricyclo[16.3.1.0^{3,8}]docosa-1(21),3,18(22),19-tetraen-17-one

Traditional Name

(7S,8S,11R,12S,15S)-7,11-dibromo-15-(2-bromopropan-2-yl)-12,21-dihydroxy-4,8,12-trimethyl-16-oxatricyclo[16.3.1.0^{3,8}]docosa-1(21),3,18(22),19-tetraen-17-one

CAS Registry Number

Not Available

SMILES

CC1=C2CC3=C(O)C=CC(=C3)C(=O)O[C@@H](CC[C@](C)(O)[C@H](Br)CC[C@]2(C)[C@@H](Br)CC1)C(C)(C)Br

InChI Identifier

InChI=1S/C27H37Br3O4/c1-16-6-9-21(28)26(4)12-10-22(29)27(5,33)13-11-23(25(2,3)30)34-24(32)17-7-8-20(31)18(14-17)15-19(16)26/h7-8,14,21-23,31,33H,6,9-13,15H2,1-5H3/t21-,22+,23-,26-,27-/m0/s1

InChI Key

SKIHYPQTROYIIT-VHXXJFIISA-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
Callophycus serratus	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Tertiary alcohol
Bromohydrin
Carboxylic acid ester
Halohydrin
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alkyl halide
Alkyl bromide
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organohalogen compound
Organobromide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary alcohol (CHEBI:65525 )
organobromine compound (CHEBI:65525 )
phenols (CHEBI:65525 )
macrolide (CHEBI:65525 )
diterpenoid (CHEBI:65525 )

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	6.89	ALOGPS
logP	7.48	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	148.59 m³·mol⁻¹	ChemAxon
Polarizability	59.51 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00041392

Chemspider ID

10480986

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21778345

PDB ID

Not Available

ChEBI ID

65525

Good Scents ID

Not Available

References

General References

Chhetri BK, Tedbury PR, Sweeney-Jones AM, Mani L, Soapi K, Manfredi C, Sorscher E, Sarafianos SG, Kubanek J: Marine Natural Products as Leads against SARS-CoV-2 Infection. J Nat Prod. 2022 Mar 25;85(3):657-665. doi: 10.1021/acs.jnatprod.2c00015. Epub 2022 Mar 15. [PubMed:35290044 ]
Teasdale ME, Prudhomme J, Torres M, Braley M, Cervantes S, Bhatia SC, La Clair JJ, Le Roch K, Kubanek J: Pharmacokinetics, metabolism, and in vivo efficacy of the antimalarial natural product bromophycolide A. ACS Med Chem Lett. 2013 Oct 10;4(10):989-993. doi: 10.1021/ml4002858. [PubMed:24159368 ]
Cervantes S, Stout PE, Prudhomme J, Engel S, Bruton M, Cervantes M, Carter D, Tae-Chang Y, Hay ME, Aalbersberg W, Kubanek J, Le Roch KG: High content live cell imaging for the discovery of new antimalarial marine natural products. BMC Infect Dis. 2012 Jan 3;12:1. doi: 10.1186/1471-2334-12-1. [PubMed:22214291 ]
Stout EP, Cervantes S, Prudhomme J, France S, La Clair JJ, Le Roch K, Kubanek J: Bromophycolide A targets heme crystallization in the human malaria parasite Plasmodium falciparum. ChemMedChem. 2011 Sep 5;6(9):1572-7. doi: 10.1002/cmdc.201100252. Epub 2011 Jul 5. [PubMed:21732541 ]
Lin H, Pochapsky SS, Krauss IJ: A short asymmetric route to the bromophycolide A and D skeleton. Org Lett. 2011 Mar 4;13(5):1222-5. doi: 10.1021/ol200099n. Epub 2011 Feb 10. [PubMed:21309525 ]

Showing NP-Card for (+)-Bromophycolide D (NP0077898)

MOL for NP0077898 ((+)-Bromophycolide D)

3D MOL for NP0077898 ((+)-Bromophycolide D)

3D SDF for NP0077898 ((+)-Bromophycolide D)

3D-SDF for NP0077898 ((+)-Bromophycolide D)

PDB for NP0077898 ((+)-Bromophycolide D)

3D PDB for NP0077898 ((+)-Bromophycolide D)

SMILES for NP0077898 ((+)-Bromophycolide D)

INCHI for NP0077898 ((+)-Bromophycolide D)

Structure for NP0077898 ((+)-Bromophycolide D)

3D Structure for NP0077898 ((+)-Bromophycolide D)