NP-MRD: Showing NP-Card for 2-[3,9-bis(acetyloxy)-1a-[(acetyloxy)methyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate (NP0205407)

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Record Information

Version

2.0

Created at

2022-09-05 01:18:45 UTC

Updated at

2022-09-05 01:18:45 UTC

NP-MRD ID

NP0205407

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

2-[8,14-Bis(acetyloxy)-11-[(acetyloxy)methyl]-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-[3,9-bis(acetyloxy)-1a-[(acetyloxy)methyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate is found in Laurencia dendroidea, Laurencia obtusa and Laurencia saitoi. 2-[8,14-Bis(acetyloxy)-11-[(acetyloxy)methyl]-1,5-dimethyltetracyclo[8.5.0.0²,⁷.0¹¹,¹³]Pentadec-2-en-5-yl]-2-bromoethyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171505452D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171505452D          

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    1.6878    3.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7765    3.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9600    3.0054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0827    3.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 28  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 15 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0205407

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC(Br)C1(C)CC=C2C(C1)C(CC1C3(COC(C)=O)CC3C(CC21C)OC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H39BrO8/c1-15(30)34-13-25(29)26(5)8-7-20-19(10-26)22(36-17(3)32)9-24-27(20,6)12-23(37-18(4)33)21-11-28(21,24)14-35-16(2)31/h7,19,21-25H,8-14H2,1-6H3

> <INCHI_KEY>
WXOXKGLRHFVTBW-UHFFFAOYSA-N

> <FORMULA>
C28H39BrO8

> <MOLECULAR_WEIGHT>
583.516

> <EXACT_MASS>
582.182831

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
57.84614648356539

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[8,14-bis(acetyloxy)-11-[(acetyloxy)methyl]-1,5-dimethyltetracyclo[8.5.0.0²,⁷.0¹¹,¹³]pentadec-2-en-5-yl]-2-bromoethyl acetate

> <ALOGPS_LOGP>
4.56

> <JCHEM_LOGP>
2.608817740666667

> <ALOGPS_LOGS>
-5.71

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.39756156033128

> <JCHEM_POLAR_SURFACE_AREA>
105.20000000000002

> <JCHEM_REFRACTIVITY>
137.4553

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[8,14-bis(acetyloxy)-11-[(acetyloxy)methyl]-1,5-dimethyltetracyclo[8.5.0.0²,⁷.0¹¹,¹³]pentadec-2-en-5-yl]-2-bromoethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      17.501   0.012   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.192   0.824   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      16.240   2.363   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      14.835   0.096   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      13.526   0.907   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.169   0.179   0.000  0.00  0.00           C+0
HETATM    7 Br   UNK     0      12.121  -1.360   0.000  0.00  0.00          Br+0
HETATM    8  C   UNK     0      10.860   0.990   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.886   2.138   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.288  -0.440   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.764  -0.660   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.812   0.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.383   1.980   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.907   2.200   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.430   3.190   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.906   2.970   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.287   0.330   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.240  -0.880   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.716  -1.100   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.192  -1.320   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.620  -2.750   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.096  -2.970   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.524  -4.400   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.143  -1.760   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.239  -0.110   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.286   1.100   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.811   1.320   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.591   2.844   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.161   3.416   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.941   4.940   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.511   5.512   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.151   5.893   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.049   5.830   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.525   5.610   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.621   7.260   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   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    8                                                       
CONECT   15   13   16   34                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   12   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   28                                                  
CONECT   27   26   28                                                       
CONECT   28   27   17   26   29                                             
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   15   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
2-[8,14-Bis(acetyloxy)-11-[(acetyloxy)methyl]-1,5-dimethyltetracyclo[8.5.0.0,.0,]pentadec-2-en-5-yl]-2-bromoethyl acetic acid	Generator
2-[8,14-Bis(acetyloxy)-11-[(acetyloxy)methyl]-1,5-dimethyltetracyclo[8.5.0.0²,⁷.0¹¹,¹³]pentadec-2-en-5-yl]-2-bromoethyl acetic acid	Generator

Chemical Formula

C₂₈H₃₉BrO₈

Average Mass

583.5160 Da

Monoisotopic Mass

582.18283 Da

IUPAC Name

2-[8,14-bis(acetyloxy)-11-[(acetyloxy)methyl]-1,5-dimethyltetracyclo[8.5.0.0²,⁷.0¹¹,¹³]pentadec-2-en-5-yl]-2-bromoethyl acetate

Traditional Name

2-[8,14-bis(acetyloxy)-11-[(acetyloxy)methyl]-1,5-dimethyltetracyclo[8.5.0.0²,⁷.0¹¹,¹³]pentadec-2-en-5-yl]-2-bromoethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC(Br)C1(C)CC=C2C(C1)C(CC1C3(COC(C)=O)CC3C(CC21C)OC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C28H39BrO8/c1-15(30)34-13-25(29)26(5)8-7-20-19(10-26)22(36-17(3)32)9-24-27(20,6)12-23(37-18(4)33)21-11-28(21,24)14-35-16(2)31/h7,19,21-25H,8-14H2,1-6H3

InChI Key

WXOXKGLRHFVTBW-UHFFFAOYSA-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 dendroidea	LOTUS Database	35616633
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
Tetracarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organobromide
Organohalogen 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	4.56	ALOGPS
logP	2.61	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	105.2 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	137.46 m³·mol⁻¹	ChemAxon
Polarizability	57.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

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

78121092

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[3,9-bis(acetyloxy)-1a-[(acetyloxy)methyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate (NP0205407)

MOL for NP0205407 (2-[3,9-bis(acetyloxy)-1a-[(acetyloxy)methyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

3D MOL for NP0205407 (2-[3,9-bis(acetyloxy)-1a-[(acetyloxy)methyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

3D SDF for NP0205407 (2-[3,9-bis(acetyloxy)-1a-[(acetyloxy)methyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

3D-SDF for NP0205407 (2-[3,9-bis(acetyloxy)-1a-[(acetyloxy)methyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

PDB for NP0205407 (2-[3,9-bis(acetyloxy)-1a-[(acetyloxy)methyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

3D PDB for NP0205407 (2-[3,9-bis(acetyloxy)-1a-[(acetyloxy)methyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

SMILES for NP0205407 (2-[3,9-bis(acetyloxy)-1a-[(acetyloxy)methyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

INCHI for NP0205407 (2-[3,9-bis(acetyloxy)-1a-[(acetyloxy)methyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

Structure for NP0205407 (2-[3,9-bis(acetyloxy)-1a-[(acetyloxy)methyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)

3D Structure for NP0205407 (2-[3,9-bis(acetyloxy)-1a-[(acetyloxy)methyl]-5,7b-dimethyl-1h,1bh,2h,3h,3ah,4h,6h,8h,9h,9ah-cyclopropa[a]phenanthren-5-yl]-2-bromoethyl acetate)