NP-MRD: Showing NP-Card for 8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate (NP0326893)

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Record Information

Version

2.0

Created at

2022-09-12 08:56:06 UTC

Updated at

2022-09-12 08:56:06 UTC

NP-MRD ID

NP0326893

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate

Description

Tubastraine belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group. 8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate is found in Tubastraea micranthus. Based on a literature review very few articles have been published on Tubastraine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122210562D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309122210562D          

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 10 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 32 38  1  0  0  0  0
 21 39  2  0  0  0  0
  6 39  1  0  0  0  0
 39 40  1  0  0  0  0
  2 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326893

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC[C@H]([C@H](C1)OC(=O)C1=CC=C(Br)C=C1)C1=C2OC(C)=CC(=O)C2=C(O)C=C1OC(=O)C1=CC=C(Br)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H25Br2NO7/c1-16-13-22(34)27-23(35)14-24(39-29(36)17-3-7-19(31)8-4-17)26(28(27)38-16)21-11-12-33(2)15-25(21)40-30(37)18-5-9-20(32)10-6-18/h3-10,13-14,21,25,35H,11-12,15H2,1-2H3/t21-,25+/m1/s1

> <INCHI_KEY>
QZBWWFYXXYZAMM-BWKNWUBXSA-N

> <FORMULA>
C30H25Br2NO7

> <MOLECULAR_WEIGHT>
671.338

> <EXACT_MASS>
668.999778

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
58.82546648795683

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[(3R,4S)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxo-4H-chromen-7-yl 4-bromobenzoate

> <JCHEM_LOGP>
6.944288525217887

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.936986486897148

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.066300626110822

> <JCHEM_PKA_STRONGEST_BASIC>
6.250142405990502

> <JCHEM_POLAR_SURFACE_AREA>
102.37000000000002

> <JCHEM_REFRACTIVITY>
157.95879999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
8-[(3R,4S)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0      14.670  -5.390   0.000  0.00  0.00          Br+0
HETATM   19  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       5.335  -7.700   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   36 Br   UNK     0       1.334 -11.550   0.000  0.00  0.00          Br+0
HETATM   37  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   39                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14                                                       
CONECT   21   10   22   39                                                  
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   38                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   32                                                       
CONECT   39   21    6   40                                                  
CONECT   40   39    2                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₅Br₂NO₇

Average Mass

671.3380 Da

Monoisotopic Mass

668.99978 Da

IUPAC Name

8-[(3R,4S)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxo-4H-chromen-7-yl 4-bromobenzoate

Traditional Name

8-[(3R,4S)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate

CAS Registry Number

Not Available

SMILES

CN1CC[C@H]([C@H](C1)OC(=O)C1=CC=C(Br)C=C1)C1=C2OC(C)=CC(=O)C2=C(O)C=C1OC(=O)C1=CC=C(Br)C=C1

InChI Identifier

InChI=1S/C30H25Br2NO7/c1-16-13-22(34)27-23(35)14-24(39-29(36)17-3-7-19(31)8-4-17)26(28(27)38-16)21-11-12-33(2)15-25(21)40-30(37)18-5-9-20(32)10-6-18/h3-10,13-14,21,25,35H,11-12,15H2,1-2H3/t21-,25+/m1/s1

InChI Key

QZBWWFYXXYZAMM-BWKNWUBXSA-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
Tubastraea micranthus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Phenylpiperidines

Direct Parent

Phenylpiperidines

Alternative Parents

Substituents

Phenylpiperidine
Chromone
Benzoate ester
Benzopyran
Phenol ester
4-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
1-benzopyran
Benzoic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Bromobenzene
Halobenzene
Phenol
Pyranone
Aralkylamine
Pyran
Aryl halide
Aryl bromide
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organohalogen compound
Organobromide
Organonitrogen 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	6.94	ChemAxon
pKa (Strongest Acidic)	7.07	ChemAxon
pKa (Strongest Basic)	6.25	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	102.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	157.96 m³·mol⁻¹	ChemAxon
Polarizability	58.83 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

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

102274178

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate (NP0326893)

MOL for NP0326893 (8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate)

3D MOL for NP0326893 (8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate)

3D SDF for NP0326893 (8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate)

3D-SDF for NP0326893 (8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate)

PDB for NP0326893 (8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate)

3D PDB for NP0326893 (8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate)

SMILES for NP0326893 (8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate)

INCHI for NP0326893 (8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate)

Structure for NP0326893 (8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate)

3D Structure for NP0326893 (8-[(3r,4s)-3-(4-bromobenzoyloxy)-1-methylpiperidin-4-yl]-5-hydroxy-2-methyl-4-oxochromen-7-yl 4-bromobenzoate)