NP-MRD: Showing NP-Card for 1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol (NP0220593)

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Record Information

Version

2.0

Created at

2022-09-05 21:57:00 UTC

Updated at

2022-09-05 21:57:00 UTC

NP-MRD ID

NP0220593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol

Description

1-Bromo-8a-(bromomethyl)-4,10a-dimethyl-8-(propan-2-yl)-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthren-4-ol 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. 1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol is found in Sphaerococcus coronopifolius. 1-Bromo-8a-(bromomethyl)-4,10a-dimethyl-8-(propan-2-yl)-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthren-4-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241509112D          

 23 25  0  0  0  0            999 V2000
   -0.9355   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   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
    1.1270   -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  0  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
    2.9202   -0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0017   -1.0659    0.0000 O   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  0  0  0  0  0  0  0  0  0  0
    4.0145   -3.4914    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  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
    2.3645   -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  0  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
    1.1270   -4.2059    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
  2  4  1  0  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  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1C=CCC2C3C(C)(O)CCC(Br)C3(C)CCC12CBr

> <INCHI_IDENTIFIER>
InChI=1S/C20H32Br2O/c1-13(2)14-6-5-7-15-17-18(3,10-11-20(14,15)12-21)16(22)8-9-19(17,4)23/h5-6,13-17,23H,7-12H2,1-4H3

> <INCHI_KEY>
HCMVLQWBPGWDHY-UHFFFAOYSA-N

> <FORMULA>
C20H32Br2O

> <MOLECULAR_WEIGHT>
448.283

> <EXACT_MASS>
446.081992

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.35196708647625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-bromo-8a-(bromomethyl)-4,10a-dimethyl-8-(propan-2-yl)-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthren-4-ol

> <ALOGPS_LOGP>
5.73

> <JCHEM_LOGP>
5.463494555999999

> <ALOGPS_LOGS>
-6.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.759531429531393

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9039809527229696

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
105.95489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.66e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1H-phenanthren-4-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -1.746  -6.517   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.206  -6.517   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564  -7.851   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.451  -1.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.737  -1.990   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0       7.494  -6.517   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.954  -6.517   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -6.517   0.000  0.00  0.00           C+0
HETATM   23 Br   UNK     0       2.104  -7.851   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    9   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    4    8   22                                             
CONECT   22   21   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂Br₂O

Average Mass

448.2830 Da

Monoisotopic Mass

446.08199 Da

IUPAC Name

1-bromo-8a-(bromomethyl)-4,10a-dimethyl-8-(propan-2-yl)-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthren-4-ol

Traditional Name

1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1H-phenanthren-4-ol

CAS Registry Number

Not Available

SMILES

CC(C)C1C=CCC2C3C(C)(O)CCC(Br)C3(C)CCC12CBr

InChI Identifier

InChI=1S/C20H32Br2O/c1-13(2)14-6-5-7-15-17-18(3,10-11-20(14,15)12-21)16(22)8-9-19(17,4)23/h5-6,13-17,23H,7-12H2,1-4H3

InChI Key

HCMVLQWBPGWDHY-UHFFFAOYSA-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
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organobromide
Organohalogen compound
Alkyl halide
Alkyl bromide
Alcohol
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	5.73	ALOGPS
logP	5.46	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	14.76	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	105.95 m³·mol⁻¹	ChemAxon
Polarizability	42.35 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol (NP0220593)

MOL for NP0220593 (1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol)

3D MOL for NP0220593 (1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol)

3D SDF for NP0220593 (1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol)

3D-SDF for NP0220593 (1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol)

PDB for NP0220593 (1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol)

3D PDB for NP0220593 (1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol)

SMILES for NP0220593 (1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol)

INCHI for NP0220593 (1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol)

Structure for NP0220593 (1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol)

3D Structure for NP0220593 (1-bromo-8a-(bromomethyl)-8-isopropyl-4,10a-dimethyl-2,3,4a,4b,5,8,9,10-octahydro-1h-phenanthren-4-ol)