NP-MRD: Showing NP-Card for (1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol (NP0298271)

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Record Information

Version

2.0

Created at

2022-09-10 09:23:31 UTC

Updated at

2022-09-10 09:23:31 UTC

NP-MRD ID

NP0298271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol

Description

(1R,5S,7R,8R,10S,11S,13R,14R)-5-[(1R)-1-bromo-2-hydroxyethyl]-11-(hydroxymethyl)-1,5-dimethyltetracyclo[8.5.0.0²,⁷.0¹¹,¹³]Pentadec-2-ene-8,14-diol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol is found in Laurencia dendroidea. Based on a literature review very few articles have been published on (1R,5S,7R,8R,10S,11S,13R,14R)-5-[(1R)-1-bromo-2-hydroxyethyl]-11-(hydroxymethyl)-1,5-dimethyltetracyclo[8.5.0.0²,⁷.0¹¹,¹³]Pentadec-2-ene-8,14-diol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309102211232D          

 25 28  0  0  1  0            999 V2000
    1.3401   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413   -0.7071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4916   -0.0920    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6840   -0.2605    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7495    0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1997    1.3068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3475   -1.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1641   -1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6744   -0.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3682   -0.1768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5517   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8786    0.4714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6951    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8178   -0.5304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9357    0.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2875    0.7965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6344   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1240   -1.2964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6137   -1.9446    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9199   -2.7107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7972   -1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -1.0607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9806   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 20 19  1  1  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  9 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END


  Mrv1652309102211232D          

 25 28  0  0  1  0            999 V2000
    1.3401   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413   -0.7071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4916   -0.0920    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6840   -0.2605    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7495    0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1997    1.3068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3475   -1.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1641   -1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6744   -0.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3682   -0.1768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5517   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8786    0.4714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6951    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8178   -0.5304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9357    0.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2875    0.7965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6344   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1240   -1.2964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6137   -1.9446    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9199   -2.7107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7972   -1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -1.0607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9806   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 20 19  1  1  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  9 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0298271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(CC=C2[C@@H](C1)[C@H](O)C[C@@H]1[C@@]3(CO)C[C@H]3[C@H](O)C[C@@]21C)[C@@H](Br)CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H31BrO4/c1-18(17(21)9-22)4-3-12-11(6-18)14(24)5-16-19(12,2)8-15(25)13-7-20(13,16)10-23/h3,11,13-17,22-25H,4-10H2,1-2H3/t11-,13+,14-,15-,16+,17+,18+,19+,20-/m1/s1

> <INCHI_KEY>
WENFBHAAQKXLBV-WNEWSIEESA-N

> <FORMULA>
C20H31BrO4

> <MOLECULAR_WEIGHT>
415.368

> <EXACT_MASS>
414.140572

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.50062588609439

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5S,7R,8R,10S,11S,13R,14R)-5-[(1R)-1-bromo-2-hydroxyethyl]-11-(hydroxymethyl)-1,5-dimethyltetracyclo[8.5.0.0^{2,7}.0^{11,13}]pentadec-2-ene-8,14-diol

> <JCHEM_LOGP>
0.8443160993333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.840200410166574

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.283816933168758

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7965395482409064

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
100.84929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S,7R,8R,10S,11S,13R,14R)-5-[(1R)-1-bromo-2-hydroxyethyl]-11-(hydroxymethyl)-1,5-dimethyltetracyclo[8.5.0.0^{2,7}.0^{11,13}]pentadec-2-ene-8,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       2.501  -2.131   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.811  -1.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.784  -0.172   0.000  0.00  0.00           C+0
HETATM    4 Br   UNK     0       1.277  -0.486   0.000  0.00  0.00          Br+0
HETATM    5  C   UNK     0       3.266   1.291   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.239   2.439   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.382  -2.750   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.906  -2.970   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.859  -1.760   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.287  -0.330   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.763  -0.110   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.240   0.880   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.764   0.660   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.860  -0.990   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.080   0.534   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.870   1.487   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.384  -1.210   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.432  -2.420   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.479  -3.630   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.050  -5.060   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.955  -3.410   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.383  -1.980   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.430  -3.190   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   24                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    2                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   19   20                                             
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   16   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23    9   15   25                                             
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₁BrO₄

Average Mass

415.3680 Da

Monoisotopic Mass

414.14057 Da

IUPAC Name

(1R,5S,7R,8R,10S,11S,13R,14R)-5-[(1R)-1-bromo-2-hydroxyethyl]-11-(hydroxymethyl)-1,5-dimethyltetracyclo[8.5.0.0^{2,7}.0^{11,13}]pentadec-2-ene-8,14-diol

Traditional Name

(1R,5S,7R,8R,10S,11S,13R,14R)-5-[(1R)-1-bromo-2-hydroxyethyl]-11-(hydroxymethyl)-1,5-dimethyltetracyclo[8.5.0.0^{2,7}.0^{11,13}]pentadec-2-ene-8,14-diol

CAS Registry Number

Not Available

SMILES

C[C@@]1(CC=C2[C@@H](C1)[C@H](O)C[C@@H]1[C@@]3(CO)C[C@H]3[C@H](O)C[C@@]21C)[C@@H](Br)CO

InChI Identifier

InChI=1S/C20H31BrO4/c1-18(17(21)9-22)4-3-12-11(6-18)14(24)5-16-19(12,2)8-15(25)13-7-20(13,16)10-23/h3,11,13-17,22-25H,4-10H2,1-2H3/t11-,13+,14-,15-,16+,17+,18+,19+,20-/m1/s1

InChI Key

WENFBHAAQKXLBV-WNEWSIEESA-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 diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Cyclic alcohol
Secondary alcohol
Halohydrin
Bromohydrin
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
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	0.84	ChemAxon
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	-0.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.85 m³·mol⁻¹	ChemAxon
Polarizability	41.5 Å³	ChemAxon
Number of Rings	4	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

12967310

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol (NP0298271)

MOL for NP0298271 ((1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol)

3D MOL for NP0298271 ((1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol)

3D SDF for NP0298271 ((1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol)

3D-SDF for NP0298271 ((1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol)

PDB for NP0298271 ((1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol)

3D PDB for NP0298271 ((1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol)

SMILES for NP0298271 ((1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol)

INCHI for NP0298271 ((1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol)

Structure for NP0298271 ((1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol)

3D Structure for NP0298271 ((1as,1bs,3r,3ar,5s,7br,9r,9ar)-5-[(1r)-1-bromo-2-hydroxyethyl]-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthrene-3,9-diol)