NP-MRD: Showing NP-Card for [(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate (NP0253656)

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Record Information

Version

2.0

Created at

2022-09-07 17:35:39 UTC

Updated at

2022-09-07 17:35:39 UTC

NP-MRD ID

NP0253656

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate

Description

(1AS,betaR)-1abeta-Acetyloxymethyl-3beta,9beta-bis(acetyloxy)-5,7bbeta-dimethyl-1a,1balpha,2,3,3abeta,4,5,6,7b,8,9,9abeta-dodecahydro-beta-bromo-1H-cyclopropa[a]phenanthrene-5beta-ethanol 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)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate is found in Laurencia obtusa and Laurencia saitoi. Based on a literature review very few articles have been published on (1aS,betaR)-1abeta-Acetyloxymethyl-3beta,9beta-bis(acetyloxy)-5,7bbeta-dimethyl-1a,1balpha,2,3,3abeta,4,5,6,7b,8,9,9abeta-dodecahydro-beta-bromo-1H-cyclopropa[a]phenanthrene-5beta-ethanol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072219352D          

 34 37  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309072219352D          

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 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 26  1  0  0  0  0
 27 26  1  1  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 34 33  1  6  0  0  0
  6 34  1  0  0  0  0
 15 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253656

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@]12C[C@H]1[C@@H](C[C@]1(C)[C@@H]2C[C@@H](OC(C)=O)[C@@H]2C[C@](C)(CC=C12)[C@@H](Br)CO)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H37BrO7/c1-14(29)32-13-26-10-19(26)21(34-16(3)31)11-25(5)18-6-7-24(4,23(27)12-28)9-17(18)20(8-22(25)26)33-15(2)30/h6,17,19-23,28H,7-13H2,1-5H3/t17-,19+,20-,21-,22+,23+,24+,25+,26-/m1/s1

> <INCHI_KEY>
OSCLQMDVZUGARH-OBWTZDJZSA-N

> <FORMULA>
C26H37BrO7

> <MOLECULAR_WEIGHT>
541.479

> <EXACT_MASS>
540.172267

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.37215951791332

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,5S,7R,8R,10S,11S,13R,14R)-8,14-bis(acetyloxy)-5-[(1R)-1-bromo-2-hydroxyethyl]-1,5-dimethyltetracyclo[8.5.0.0^{2,7}.0^{11,13}]pentadec-2-en-11-yl]methyl acetate

> <JCHEM_LOGP>
2.167692330333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.505793175176066

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0149660651779877

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
128.3038

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,5S,7R,8R,10S,11S,13R,14R)-8,14-bis(acetyloxy)-5-[(1R)-1-bromo-2-hydroxyethyl]-1,5-dimethyltetracyclo[8.5.0.0^{2,7}.0^{11,13}]pentadec-2-en-11-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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       4.901 -10.894   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.691  -9.941   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.261 -10.513   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.911  -8.417   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.701  -7.464   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.921  -5.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.397  -5.720   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.350  -4.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.302  -3.300   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.731  -1.870   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.207  -1.650   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.254  -2.860   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.635  -0.220   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.827  -3.520   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.398  -4.950   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.351  -3.740   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.922  -5.170   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.875  -3.960   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.399  -4.180   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.971  -5.610   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.280  -4.799   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.997  -6.758   0.000  0.00  0.00           C+0
HETATM   23 Br   UNK     0      10.516  -8.221   0.000  0.00  0.00          Br+0
HETATM   24  C   UNK     0      12.505  -6.444   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.986  -4.981   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.018  -6.820   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.494  -6.600   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.541  -7.810   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.113  -9.240   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.637  -9.460   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.590  -8.250   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.209 -10.890   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.017  -7.590   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.446  -6.160   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   34                                             
CONECT    7    6    8                                                       
CONECT    8    7    6    9                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16   17   34                                             
CONECT   16   15                                                            
CONECT   17   15   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   26                                             
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   20   27                                                       
CONECT   27   26   17   28                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34                                                       
CONECT   34   33    6   15                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(1AS,betar)-1abeta-acetyloxymethyl-3b,9b-bis(acetyloxy)-5,7bbeta-dimethyl-1a,1balpha,2,3,3abeta,4,5,6,7b,8,9,9abeta-dodecahydro-b-bromo-1H-cyclopropa[a]phenanthrene-5b-ethanol	Generator
(1AS,betar)-1abeta-acetyloxymethyl-3β,9β-bis(acetyloxy)-5,7bbeta-dimethyl-1a,1balpha,2,3,3abeta,4,5,6,7b,8,9,9abeta-dodecahydro-β-bromo-1H-cyclopropa[a]phenanthrene-5β-ethanol	Generator

Chemical Formula

C₂₆H₃₇BrO₇

Average Mass

541.4790 Da

Monoisotopic Mass

540.17227 Da

IUPAC Name

[(1R,5S,7R,8R,10S,11S,13R,14R)-8,14-bis(acetyloxy)-5-[(1R)-1-bromo-2-hydroxyethyl]-1,5-dimethyltetracyclo[8.5.0.0^{2,7}.0^{11,13}]pentadec-2-en-11-yl]methyl acetate

Traditional Name

[(1R,5S,7R,8R,10S,11S,13R,14R)-8,14-bis(acetyloxy)-5-[(1R)-1-bromo-2-hydroxyethyl]-1,5-dimethyltetracyclo[8.5.0.0^{2,7}.0^{11,13}]pentadec-2-en-11-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@]12C[C@H]1[C@@H](C[C@]1(C)[C@@H]2C[C@@H](OC(C)=O)[C@@H]2C[C@](C)(CC=C12)[C@@H](Br)CO)OC(C)=O

InChI Identifier

InChI=1S/C26H37BrO7/c1-14(29)32-13-26-10-19(26)21(34-16(3)31)11-25(5)18-6-7-24(4,23(27)12-28)9-17(18)20(8-22(25)26)33-15(2)30/h6,17,19-23,28H,7-13H2,1-5H3/t17-,19+,20-,21-,22+,23+,24+,25+,26-/m1/s1

InChI Key

OSCLQMDVZUGARH-OBWTZDJZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Laurencia obtusa	LOTUS Database	35616633
Laurencia saitoi	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
Tricarboxylic acid or derivatives
Bromohydrin
Carboxylic acid ester
Halohydrin
Carboxylic acid derivative
Organooxygen compound
Organobromide
Organohalogen compound
Alkyl bromide
Organic oxygen compound
Carbonyl group
Alcohol
Alkyl halide
Primary alcohol
Organic oxide
Hydrocarbon derivative
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	2.17	ChemAxon
pKa (Strongest Acidic)	14.51	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	128.3 m³·mol⁻¹	ChemAxon
Polarizability	54.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

27023427

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101589001

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)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate (NP0253656)

MOL for NP0253656 ([(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate)

3D MOL for NP0253656 ([(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate)

3D SDF for NP0253656 ([(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate)

3D-SDF for NP0253656 ([(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate)

PDB for NP0253656 ([(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate)

3D PDB for NP0253656 ([(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate)

SMILES for NP0253656 ([(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate)

INCHI for NP0253656 ([(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate)

Structure for NP0253656 ([(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate)

3D Structure for NP0253656 ([(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-5-[(1r)-1-bromo-2-hydroxyethyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-1a-yl]methyl acetate)