NP-MRD: Showing NP-Card for (2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine (NP0323255)

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Record Information

Version

2.0

Created at

2022-09-12 02:33:34 UTC

Updated at

2022-09-12 02:33:34 UTC

NP-MRD ID

NP0323255

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine

Description

(2R,6R)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]Dodeca-1(8),9,11-trien-12-amine belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. (2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine is found in Flustra foliacea. Based on a literature review very few articles have been published on (2R,6R)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]Dodeca-1(8),9,11-trien-12-amine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122204332D          

 25 27  0  0  1  0            999 V2000
    7.8649    2.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0615    2.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8221    1.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4975    2.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6941    2.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4546    1.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0186    1.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792    0.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3432   -0.1242    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.9758    0.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7364   -0.4991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4118    0.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512    1.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9743    2.1537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3166    1.6557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4917    1.6395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9938    2.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2523    0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292    0.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5869    0.8763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8573    0.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175   -0.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5073   -0.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9674   -0.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2369    0.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END


  Mrv1652309122204332D          

 25 27  0  0  1  0            999 V2000
    7.8649    2.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0615    2.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8221    1.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4975    2.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6941    2.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4546    1.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0186    1.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792    0.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3432   -0.1242    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.9758    0.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7364   -0.4991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4118    0.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512    1.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9743    2.1537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3166    1.6557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4917    1.6395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9938    2.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2523    0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292    0.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5869    0.8763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8573    0.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175   -0.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5073   -0.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9674   -0.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2369    0.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0323255

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC[C@@]2(CC=C(C)C)[C@H]1OC1=C2C(N)=C(Br)C=C1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C21H29BrN2O/c1-13(2)6-7-15-12-16(22)18(23)17-19(15)25-20-21(17,9-8-14(3)4)10-11-24(20)5/h6,8,12,20H,7,9-11,23H2,1-5H3/t20-,21-/m1/s1

> <INCHI_KEY>
SQMRGQPMSRIJKQ-NHCUHLMSSA-N

> <FORMULA>
C21H29BrN2O

> <MOLECULAR_WEIGHT>
405.38

> <EXACT_MASS>
404.146327

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.22372841471468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,6R)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0^{2,6}]dodeca-1(8),9,11-trien-12-amine

> <JCHEM_LOGP>
5.352965723333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.413109262491868

> <JCHEM_POLAR_SURFACE_AREA>
38.49

> <JCHEM_REFRACTIVITY>
111.49319999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,6R)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0^{2,6}]dodeca-1(8),9,11-trien-12-amine

> <JCHEM_VEBER_RULE>
1

$$$$

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      14.681   4.539   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.181   4.189   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.735   2.716   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.129   5.313   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.629   4.963   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.182   3.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.235   2.366   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.788   0.892   0.000  0.00  0.00           C+0
HETATM    9 Br   UNK     0      11.841  -0.232   0.000  0.00  0.00          Br+0
HETATM   10  C   UNK     0       9.288   0.542   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       8.841  -0.932   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       8.235   1.666   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.682   3.140   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.419   4.020   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.191   3.091   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.651   3.060   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.722   4.288   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.204   1.587   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.468   0.706   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.696   1.636   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.200   0.181   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.193  -0.984   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.680  -0.693   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.673  -1.858   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.176   0.762   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20                                                  
CONECT   13   12    6   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   12   15   21                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₉BrN₂O

Average Mass

405.3800 Da

Monoisotopic Mass

404.14633 Da

IUPAC Name

(2R,6R)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0^{2,6}]dodeca-1(8),9,11-trien-12-amine

Traditional Name

(2R,6R)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0^{2,6}]dodeca-1(8),9,11-trien-12-amine

CAS Registry Number

Not Available

SMILES

CN1CC[C@@]2(CC=C(C)C)[C@H]1OC1=C2C(N)=C(Br)C=C1CC=C(C)C

InChI Identifier

InChI=1S/C21H29BrN2O/c1-13(2)6-7-15-12-16(22)18(23)17-19(15)25-20-21(17,9-8-14(3)4)10-11-24(20)5/h6,8,12,20H,7,9-11,23H2,1-5H3/t20-,21-/m1/s1

InChI Key

SQMRGQPMSRIJKQ-NHCUHLMSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Flustra foliacea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

Alternative Parents

Substituents

Coumaran
2-bromoaniline
Benzenoid
N-alkylpyrrolidine
Aryl halide
Aryl bromide
Pyrrolidine
Oxacycle
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Amine
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	5.35	ChemAxon
pKa (Strongest Basic)	5.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.49 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111.49 m³·mol⁻¹	ChemAxon
Polarizability	42.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

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

163034721

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine (NP0323255)

MOL for NP0323255 ((2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine)

3D MOL for NP0323255 ((2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine)

3D SDF for NP0323255 ((2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine)

3D-SDF for NP0323255 ((2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine)

PDB for NP0323255 ((2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine)

3D PDB for NP0323255 ((2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine)

SMILES for NP0323255 ((2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine)

INCHI for NP0323255 ((2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine)

Structure for NP0323255 ((2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine)

3D Structure for NP0323255 ((2r,6r)-11-bromo-5-methyl-2,9-bis(3-methylbut-2-en-1-yl)-7-oxa-5-azatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-trien-12-amine)