NP-MRD: Showing NP-Card for 6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate (NP0250304)

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Record Information

Version

2.0

Created at

2022-09-07 13:05:36 UTC

Updated at

2022-09-07 13:05:36 UTC

NP-MRD ID

NP0250304

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate

Description

6,9-Dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]Tridec-11-en-7-yl acetate belongs to the class of organic compounds known as dihydrofurans. Dihydrofurans are compounds containing a dihydrofuran moiety, which is a furan derivative with only one double bond. 6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate is found in Laurencia dendroidea. 6,9-Dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]Tridec-11-en-7-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191517352D          

 25 26  0  0  0  0            999 V2000
    5.0221    0.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2157    0.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6617    0.3007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7718    0.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560    0.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447    0.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7827    1.3491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5440    2.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0183    2.8556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7275    1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    0.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980    2.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456    3.6166    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.9044    2.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569    1.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7108    2.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4584    3.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0124    3.8797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    3.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633    1.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5173    2.3088    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.9159   -0.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2845   -0.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531   -1.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972   -2.2338    0.0000 Br  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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
M  END


  Mrv1533004191517352D          

 25 26  0  0  0  0            999 V2000
    5.0221    0.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2157    0.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6617    0.3007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7718    0.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560    0.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447    0.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7827    1.3491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5440    2.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0183    2.8556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7275    1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    0.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980    2.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456    3.6166    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.9044    2.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569    1.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7108    2.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4584    3.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0124    3.8797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    3.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633    1.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5173    2.3088    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.9159   -0.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2845   -0.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531   -1.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972   -2.2338    0.0000 Br  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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0250304

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(CC2OC(O)(C=C2)C(Br)CC(OC(C)=O)C1Br)C=C=CBr

> <INCHI_IDENTIFIER>
InChI=1S/C17H21Br3O5/c1-10-16(20)14(24-11(2)21)9-15(19)17(22)6-5-13(25-17)8-12(23-10)4-3-7-18/h4-7,10,12-16,22H,8-9H2,1-2H3

> <INCHI_KEY>
QMIYKLOJFDAYFZ-UHFFFAOYSA-N

> <FORMULA>
C17H21Br3O5

> <MOLECULAR_WEIGHT>
545.062

> <EXACT_MASS>
541.893913

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
42.450380258841165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
3.868223502666665

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.743029567581376

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9966044946980177

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
105.23610000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       9.375   1.378   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.869   1.703   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.835   0.561   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.174   0.845   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.838   0.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.697   1.114   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.328   2.518   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.882   4.144   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.901   5.331   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.358   3.215   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.264   1.678   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.916   5.285   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       3.445   6.751   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0       5.422   4.960   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.893   3.494   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.927   4.635   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.456   6.101   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.490   7.242   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.950   6.426   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.398   3.169   0.000  0.00  0.00           C+0
HETATM   21 Br   UNK     0       8.432   4.310   0.000  0.00  0.00          Br+0
HETATM   22  C   UNK     0       5.443  -0.671   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.264  -1.662   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.086  -2.653   0.000  0.00  0.00           C+0
HETATM   25 Br   UNK     0       3.355  -4.170   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   12                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    6                                                       
CONECT   12    8   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15    2   21                                                  
CONECT   21   20                                                            
CONECT   22    4   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
6,9-Dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₁Br₃O₅

Average Mass

545.0620 Da

Monoisotopic Mass

541.89391 Da

IUPAC Name

6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate

Traditional Name

6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate

CAS Registry Number

Not Available

SMILES

CC1OC(CC2OC(O)(C=C2)C(Br)CC(OC(C)=O)C1Br)C=C=CBr

InChI Identifier

InChI=1S/C17H21Br3O5/c1-10-16(20)14(24-11(2)21)9-15(19)17(22)6-5-13(25-17)8-12(23-10)4-3-7-18/h4-7,10,12-16,22H,8-9H2,1-2H3

InChI Key

QMIYKLOJFDAYFZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Laurencia dendroidea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydrofurans. Dihydrofurans are compounds containing a dihydrofuran moiety, which is a furan derivative with only one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Not Available

Direct Parent

Dihydrofurans

Alternative Parents

Substituents

Dihydrofuran
Bromohydrin
Carboxylic acid ester
Halohydrin
Hemiacetal
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Vinyl halide
Monocarboxylic acid or derivatives
Vinyl bromide
Alkyl halide
Hydrocarbon derivative
Alkyl bromide
Organic oxygen compound
Carbonyl group
Organohalogen compound
Organobromide
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.81	ALOGPS
logP	3.87	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	10.74	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.24 m³·mol⁻¹	ChemAxon
Polarizability	42.45 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

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

73657600

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate (NP0250304)

MOL for NP0250304 (6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate)

3D MOL for NP0250304 (6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate)

3D SDF for NP0250304 (6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate)

3D-SDF for NP0250304 (6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate)

PDB for NP0250304 (6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate)

3D PDB for NP0250304 (6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate)

SMILES for NP0250304 (6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate)

INCHI for NP0250304 (6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate)

Structure for NP0250304 (6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate)

3D Structure for NP0250304 (6,9-dibromo-3-(3-bromopropa-1,2-dien-1-yl)-10-hydroxy-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-11-en-7-yl acetate)