NP-MRD: Showing NP-Card for (1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol (NP0223459)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 01:33:59 UTC

Updated at

2022-09-06 01:33:59 UTC

NP-MRD ID

NP0223459

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol

Description

Neorogioldiol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol is found in Laurencia obtusa. (1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol was first documented in 2019 (PMID: 30717366). Based on a literature review very few articles have been published on Neorogioldiol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062203342D          

 24 26  0  0  1  0            999 V2000
   -1.7224   -1.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2549   -2.1195    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1765   -1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4062   -2.1436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1631    0.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6073    0.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224    0.0470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5474    0.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9599    0.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5474    1.4760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3227    1.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4042    2.2884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224    1.4760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3099    2.1904    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    0.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  4  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
  7 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16  2  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 16 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223459

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H]2CC[C@@](C)(O)[C@@H]2[C@@H](Br)[C@@H]1C(=C)[C@@H]1CC[C@](C)(O)[C@H](Br)C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H32Br2O2/c1-11(12-6-8-19(4,23)14(21)10-12)15-17(22)16-13(18(15,2)3)7-9-20(16,5)24/h12-17,23-24H,1,6-10H2,2-5H3/t12-,13-,14-,15+,16+,17+,19+,20-/m1/s1

> <INCHI_KEY>
ARJJMSRVKBBKMI-WLMMIMMTSA-N

> <FORMULA>
C20H32Br2O2

> <MOLECULAR_WEIGHT>
464.282

> <EXACT_MASS>
462.076906

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.31683101863812

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3aR,5S,6S,6aR)-6-bromo-5-{1-[(1R,3R,4S)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-octahydropentalen-1-ol

> <JCHEM_LOGP>
4.2410519696666675

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.823360086953056

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.970442213210116

> <JCHEM_PKA_STRONGEST_BASIC>
-2.911183559666033

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
106.01339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3aR,5S,6S,6aR)-6-bromo-5-{1-[(1R,3R,4S)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.215  -2.580   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.445  -1.246   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.905  -1.246   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM    5 Br   UNK     0      -0.476  -3.956   0.000  0.00  0.00          Br+0
HETATM    6  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.063  -3.534   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.625  -4.001   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.304   1.510   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.134   1.042   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.215   0.088   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.755   0.088   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.525   1.421   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.755   2.755   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.202   3.282   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.488   4.272   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.215   2.755   0.000  0.00  0.00           C+0
HETATM   23 Br   UNK     0      -2.445   4.089   0.000  0.00  0.00          Br+0
HETATM   24  C   UNK     0      -2.445   1.421   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11   12                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7    3   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    2   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂Br₂O₂

Average Mass

464.2820 Da

Monoisotopic Mass

462.07691 Da

IUPAC Name

(1R,3aR,5S,6S,6aR)-6-bromo-5-{1-[(1R,3R,4S)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-octahydropentalen-1-ol

Traditional Name

(1R,3aR,5S,6S,6aR)-6-bromo-5-{1-[(1R,3R,4S)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol

CAS Registry Number

Not Available

SMILES

CC1(C)[C@@H]2CC[C@@](C)(O)[C@@H]2[C@@H](Br)[C@@H]1C(=C)[C@@H]1CC[C@](C)(O)[C@H](Br)C1

InChI Identifier

InChI=1S/C20H32Br2O2/c1-11(12-6-8-19(4,23)14(21)10-12)15-17(22)16-13(18(15,2)3)7-9-20(16,5)24/h12-17,23-24H,1,6-10H2,2-5H3/t12-,13-,14-,15+,16+,17+,19+,20-/m1/s1

InChI Key

ARJJMSRVKBBKMI-WLMMIMMTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Laurencia obtusa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Bisabolane sesquiterpenoid
Sesquiterpenoid
Cyclohexyl halide
Cyclohexanol
Cyclic alcohol
Tertiary alcohol
Bromohydrin
Halohydrin
Organohalogen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Alkyl halide
Alkyl bromide
Organobromide
Organooxygen compound
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	4.24	ChemAxon
pKa (Strongest Acidic)	13.97	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	106.01 m³·mol⁻¹	ChemAxon
Polarizability	43.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

12113782

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Daskalaki MG, Vyrla D, Harizani M, Doxaki C, Eliopoulos AG, Roussis V, Ioannou E, Tsatsanis C, Kampranis SC: Neorogioltriol and Related Diterpenes from the Red Alga Laurencia Inhibit Inflammatory Bowel Disease in Mice by Suppressing M1 and Promoting M2-Like Macrophage Responses. Mar Drugs. 2019 Feb 2;17(2):97. doi: 10.3390/md17020097. [PubMed:30717366 ]
LOTUS database [Link]

Showing NP-Card for (1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol (NP0223459)

MOL for NP0223459 ((1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol)

3D MOL for NP0223459 ((1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol)

3D SDF for NP0223459 ((1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol)

3D-SDF for NP0223459 ((1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol)

PDB for NP0223459 ((1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol)

3D PDB for NP0223459 ((1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol)

SMILES for NP0223459 ((1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol)

INCHI for NP0223459 ((1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol)

Structure for NP0223459 ((1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol)

3D Structure for NP0223459 ((1r,3ar,5s,6s,6ar)-6-bromo-5-{1-[(1r,3r,4s)-3-bromo-4-hydroxy-4-methylcyclohexyl]ethenyl}-1,4,4-trimethyl-hexahydropentalen-1-ol)