NP-MRD: Showing NP-Card for 2-[(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate (NP0329823)

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Record Information

Version

2.0

Created at

2022-09-12 14:35:45 UTC

Updated at

2022-09-12 14:35:45 UTC

NP-MRD ID

NP0329823

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

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

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122216352D          

 34 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652309122216352D          

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 15 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 26 25  1  1  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
 12 33  1  0  0  0  0
 21 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0329823

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
DLVSGIMHXFEYFH-LYXQNHFHSA-N

> <FORMULA>
C26H37BrO7

> <MOLECULAR_WEIGHT>
541.479

> <EXACT_MASS>
540.172267

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.2790403990604

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
2.167692330333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.086417964400319

> <JCHEM_PKA_STRONGEST_BASIC>
-2.761000782371301

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
128.3038

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.021  -6.832   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.289  -6.021   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.646  -6.749   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.240  -4.482   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.550  -3.670   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.501  -2.131   0.000  0.00  0.00           C+0
HETATM    7 Br   UNK     0       1.144  -1.403   0.000  0.00  0.00          Br+0
HETATM    8  C   UNK     0       3.811  -1.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.784  -0.172   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.382  -2.750   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.906  -2.970   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.859  -1.760   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.287  -0.330   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.763  -0.110   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.240   0.880   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.144   2.530   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.192   1.320   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.573   3.960   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.764   0.660   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.860  -0.990   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.080   0.534   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.510   1.106   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.384  -1.210   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.432  -2.420   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.479  -3.630   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.050  -5.060   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.575  -5.280   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.527  -4.070   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.146  -6.710   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.955  -3.410   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.383  -1.980   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.430  -3.190   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                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    8                                                       
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22   33                                                  
CONECT   22   21   23   25   26                                             
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   22   27                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27   33                                                       
CONECT   33   32   12   21   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
2-[(1R,5S,7R,8R,10S,11S,13R,14R)-8,14-Bis(acetyloxy)-11-(hydroxymethyl)-1,5-dimethyltetracyclo[8.5.0.0,.0,]pentadec-2-en-5-yl]-2-bromoethyl acetic acid	Generator

Chemical Formula

C₂₆H₃₇BrO₇

Average Mass

541.4790 Da

Monoisotopic Mass

540.17227 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

DLVSGIMHXFEYFH-LYXQNHFHSA-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
Jania rubens	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
Carboxylic acid ester
Carboxylic acid derivative
Alcohol
Primary alcohol
Organooxygen compound
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.17	ChemAxon
pKa (Strongest Acidic)	15.09	ChemAxon
pKa (Strongest Basic)	-2.8	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	54.28 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

8991605

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10816301

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate (NP0329823)

MOL for NP0329823 (2-[(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

3D MOL for NP0329823 (2-[(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

3D SDF for NP0329823 (2-[(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

3D-SDF for NP0329823 (2-[(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

PDB for NP0329823 (2-[(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

3D PDB for NP0329823 (2-[(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

SMILES for NP0329823 (2-[(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

INCHI for NP0329823 (2-[(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

Structure for NP0329823 (2-[(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

3D Structure for NP0329823 (2-[(1as,1bs,3r,3ar,5s,7br,9r,9ar)-3,9-bis(acetyloxy)-1a-(hydroxymethyl)-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)