NP-MRD: Showing NP-Card for (11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one (NP0190988)

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Record Information

Version

2.0

Created at

2022-09-04 07:46:39 UTC

Updated at

2022-09-04 07:46:39 UTC

NP-MRD ID

NP0190988

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one

Description

Bromophycolide K 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. (11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one is found in Callophycus serratus. Based on a literature review very few articles have been published on Bromophycolide K.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042209462D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042209462D          

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M  END
> <DATABASE_ID>
NP0190988

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2CC3=CC(=CC=C3O)C(=O)O[C@@H](CC[C@](C)(O)[C@H](Br)CCC2C(=C)CC1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H37BrO5/c1-16-6-7-17(2)21-15-19-14-18(8-10-22(19)29)25(30)33-24(26(3,4)31)12-13-27(5,32)23(28)11-9-20(16)21/h8,10,14,20,23-24,29,31-32H,1,6-7,9,11-13,15H2,2-5H3/t20?,23-,24+,27+/m1/s1

> <INCHI_KEY>
LWYZNBXETNJHDW-OBWQYEKRSA-N

> <FORMULA>
C27H37BrO5

> <MOLECULAR_WEIGHT>
521.492

> <EXACT_MASS>
520.182437

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.6331017202673

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11R,12S,15S)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0^{3,8}]docosa-1(22),3,18,20-tetraen-17-one

> <JCHEM_LOGP>
5.2720583843333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.855695317124681

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.297321220555647

> <JCHEM_PKA_STRONGEST_BASIC>
-3.10408489281225

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
134.8601

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(11R,12S,15S)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0^{3,8}]docosa-1(22),3,18,20-tetraen-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.688  -3.025   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.363  -2.239   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.381  -0.699   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.057   0.086   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.286  -0.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.611   0.118   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.304  -2.208   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.826  -0.759   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.365  -0.808   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.795  -2.287   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.187  -3.236   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.198  -2.018   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.014  -0.489   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.597   0.116   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.413   1.645   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.138  -4.776   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.781  -5.503   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.447  -5.588   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.398  -7.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.706  -7.939   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.015  -8.750   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.895  -9.247   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.518  -6.630   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.040  -7.854   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.732  -7.042   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.374  -7.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.326  -8.980   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.348  -8.917   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.066  -6.958   0.000  0.00  0.00           C+0
HETATM   30 Br   UNK     0      -0.292  -7.685   0.000  0.00  0.00          Br+0
HETATM   31  C   UNK     0       1.115  -5.419   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.194  -4.607   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.020  -2.993   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   33                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   11   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   19   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₇BrO₅

Average Mass

521.4920 Da

Monoisotopic Mass

520.18244 Da

IUPAC Name

(11R,12S,15S)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0^{3,8}]docosa-1(22),3,18,20-tetraen-17-one

Traditional Name

(11R,12S,15S)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0^{3,8}]docosa-1(22),3,18,20-tetraen-17-one

CAS Registry Number

Not Available

SMILES

CC1=C2CC3=CC(=CC=C3O)C(=O)O[C@@H](CC[C@](C)(O)[C@H](Br)CCC2C(=C)CC1)C(C)(C)O

InChI Identifier

InChI=1S/C27H37BrO5/c1-16-6-7-17(2)21-15-19-14-18(8-10-22(19)29)25(30)33-24(26(3,4)31)12-13-27(5,32)23(28)11-9-20(16)21/h8,10,14,20,23-24,29,31-32H,1,6-7,9,11-13,15H2,2-5H3/t20?,23-,24+,27+/m1/s1

InChI Key

LWYZNBXETNJHDW-OBWQYEKRSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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	LOTUS Database	35616633

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
Phenol
Benzenoid
Tertiary alcohol
Bromohydrin
Carboxylic acid ester
Halohydrin
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
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

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	5.27	ChemAxon
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	134.86 m³·mol⁻¹	ChemAxon
Polarizability	52.63 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

Not Available

Chemspider ID

27024131

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42599771

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one (NP0190988)

MOL for NP0190988 ((11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one)

3D MOL for NP0190988 ((11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one)

3D SDF for NP0190988 ((11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one)

3D-SDF for NP0190988 ((11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one)

PDB for NP0190988 ((11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one)

3D PDB for NP0190988 ((11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one)

SMILES for NP0190988 ((11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one)

INCHI for NP0190988 ((11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one)

Structure for NP0190988 ((11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one)

3D Structure for NP0190988 ((11r,12s,15s)-11-bromo-12,21-dihydroxy-15-(2-hydroxypropan-2-yl)-4,12-dimethyl-7-methylidene-16-oxatricyclo[16.3.1.0³,⁸]docosa-1(22),3,18,20-tetraen-17-one)