NP-MRD: Showing NP-Card for (1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene (NP0250081)

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Record Information

Version

2.0

Created at

2022-09-07 12:49:25 UTC

Updated at

2022-09-07 12:49:25 UTC

NP-MRD ID

NP0250081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene

Description

Bromosphaeren A belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation. (1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene is found in Sphaerococcus coronopifolius. Based on a literature review very few articles have been published on Bromosphaeren A.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072214492D          

 22 24  0  0  1  0            999 V2000
    1.5395   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -4.2059    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  8 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0250081

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1CC=C[C@H]2C3=C(C)CC[C@H](Br)[C@@]3(C)CC[C@]12CBr

> <INCHI_IDENTIFIER>
InChI=1S/C20H30Br2/c1-13(2)15-6-5-7-16-18-14(3)8-9-17(22)19(18,4)10-11-20(15,16)12-21/h5,7,13,15-17H,6,8-12H2,1-4H3/t15-,16-,17-,19+,20-/m0/s1

> <INCHI_KEY>
CZKXKBOZYSPRSB-CAVMOMJPSA-N

> <FORMULA>
C20H30Br2

> <MOLECULAR_WEIGHT>
430.268

> <EXACT_MASS>
428.071427

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
40.7364762589482

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4bS,8S,8aS,10aS)-1-bromo-8a-(bromomethyl)-4,10a-dimethyl-8-(propan-2-yl)-1,2,3,4b,7,8,8a,9,10,10a-decahydrophenanthrene

> <JCHEM_LOGP>
6.329464475

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
104.8562

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4bS,8S,8aS,10aS)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.874  -1.183   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.494  -6.517   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034  -6.517   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.724  -7.851   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.954  -6.517   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0       5.184  -7.851   0.000  0.00  0.00          Br+0
HETATM   15  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -6.517   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM   20 Br   UNK     0      -0.206  -6.517   0.000  0.00  0.00          Br+0
HETATM   21  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8    4   13   15                                             
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    3   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀Br₂

Average Mass

430.2680 Da

Monoisotopic Mass

428.07143 Da

IUPAC Name

(1S,4bS,8S,8aS,10aS)-1-bromo-8a-(bromomethyl)-4,10a-dimethyl-8-(propan-2-yl)-1,2,3,4b,7,8,8a,9,10,10a-decahydrophenanthrene

Traditional Name

(1S,4bS,8S,8aS,10aS)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1CC=C[C@H]2C3=C(C)CC[C@H](Br)[C@@]3(C)CC[C@]12CBr

InChI Identifier

InChI=1S/C20H30Br2/c1-13(2)15-6-5-7-16-18-14(3)8-9-17(22)19(18,4)10-11-20(15,16)12-21/h5,7,13,15-17H,6,8-12H2,1-4H3/t15-,16-,17-,19+,20-/m0/s1

InChI Key

CZKXKBOZYSPRSB-CAVMOMJPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sphaerococcus coronopifolius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Hydrophenanthrenes

Direct Parent

Hydrophenanthrenes

Alternative Parents

Substituents

Hydrophenanthrene
Hydrocarbon derivative
Organobromide
Organohalogen compound
Alkyl halide
Alkyl bromide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	6.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.86 m³·mol⁻¹	ChemAxon
Polarizability	40.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

27026233

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101318105

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene (NP0250081)

MOL for NP0250081 ((1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene)

3D MOL for NP0250081 ((1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene)

3D SDF for NP0250081 ((1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene)

3D-SDF for NP0250081 ((1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene)

PDB for NP0250081 ((1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene)

3D PDB for NP0250081 ((1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene)

SMILES for NP0250081 ((1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene)

INCHI for NP0250081 ((1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene)

Structure for NP0250081 ((1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene)

3D Structure for NP0250081 ((1s,4bs,8s,8as,10as)-1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-1,2,3,4b,7,8,9,10-octahydrophenanthrene)