NP-MRD: Showing NP-Card for 6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol (NP0292836)

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Record Information

Version

2.0

Created at

2022-09-10 00:33:51 UTC

Updated at

2022-09-10 00:33:51 UTC

NP-MRD ID

NP0292836

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol

Description

6-Bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]Hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol is found in Chondria armata. 6-Bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]Hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171519072D          

 37 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171519072D          

 37 40  0  0  0  0            999 V2000
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   -3.0933   -3.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3987   -3.3817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0975   -3.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2890   -2.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0797   -1.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789   -2.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4257   -2.2034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1654   -2.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9898   -1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6861   -1.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5111   -1.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0191   -2.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8276   -3.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6525   -3.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0032   -4.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0808   -3.7400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3410   -3.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203   -4.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954   -4.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4874   -3.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2364   -4.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6967   -3.5918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 21 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 18 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292836

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)(CCC1OC(C)(C)C(Br)CCC1(C)O)C1CCC2OC3(C)CC=CC(C)(C)OC3CCC2(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C30H51BrO6/c1-25(2)15-9-16-29(7)24(34-25)14-19-30(8)23(37-29)11-10-21(36-30)28(6,33)18-13-22-27(5,32)17-12-20(31)26(3,4)35-22/h9,15,20-24,32-33H,10-14,16-19H2,1-8H3

> <INCHI_KEY>
GOJQGQABYBPKGL-UHFFFAOYSA-N

> <FORMULA>
C30H51BrO6

> <MOLECULAR_WEIGHT>
587.636

> <EXACT_MASS>
586.286902

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
63.26614623872109

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol

> <ALOGPS_LOGP>
5.25

> <JCHEM_LOGP>
4.946984426999998

> <ALOGPS_LOGS>
-5.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.353778418577622

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.751529350688248

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2125979194299177

> <JCHEM_POLAR_SURFACE_AREA>
77.38000000000001

> <JCHEM_REFRACTIVITY>
149.9906

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.07e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol

> <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      -0.855  -7.561   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.294  -6.085   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.733  -4.609   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.770  -6.525   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.128  -8.023   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.604  -8.462   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.848  -9.983   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.189 -10.739   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.153 -11.879   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.069 -12.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.617 -10.163   0.000  0.00  0.00           C+0
HETATM   12 Br   UNK     0      -8.756 -11.199   0.000  0.00  0.00          Br+0
HETATM   13  C   UNK     0      -8.057  -8.687   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.177  -7.423   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.640  -7.323   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.774  -5.789   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.478  -6.313   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.182  -5.646   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.539  -4.148   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.015  -3.709   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.134  -4.767   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.528  -4.113   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.909  -4.795   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.581  -3.290   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.881  -3.600   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.421  -3.616   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.369  -4.829   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.011  -6.327   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.551  -6.342   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.339  -7.832   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.617  -6.981   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.237  -6.299   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.265  -7.494   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.725  -7.479   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.776  -6.265   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.308  -7.732   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.300  -6.705   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   18                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    6   16   17                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    2   19   37                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   35                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25   32                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   32                                                       
CONECT   32   31   23   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   21   36   37                                             
CONECT   36   35                                                            
CONECT   37   35   18                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₁BrO₆

Average Mass

587.6360 Da

Monoisotopic Mass

586.28690 Da

IUPAC Name

6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol

Traditional Name

6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol

CAS Registry Number

Not Available

SMILES

CC(O)(CCC1OC(C)(C)C(Br)CCC1(C)O)C1CCC2OC3(C)CC=CC(C)(C)OC3CCC2(C)O1

InChI Identifier

InChI=1S/C30H51BrO6/c1-25(2)15-9-16-29(7)24(34-25)14-19-30(8)23(37-29)11-10-21(36-30)28(6,33)18-13-22-27(5,32)17-12-20(31)26(3,4)35-22/h9,15,20-24,32-33H,10-14,16-19H2,1-8H3

InChI Key

GOJQGQABYBPKGL-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
Chondria armata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Oxepane
Oxane
Tertiary alcohol
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organobromide
Organohalogen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Alkyl bromide
Alkyl halide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	5.25	ALOGPS
logP	4.95	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.38 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	149.99 m³·mol⁻¹	ChemAxon
Polarizability	63.27 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	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

78163248

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol (NP0292836)

MOL for NP0292836 (6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol)

3D MOL for NP0292836 (6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol)

3D SDF for NP0292836 (6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol)

3D-SDF for NP0292836 (6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol)

PDB for NP0292836 (6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol)

3D PDB for NP0292836 (6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol)

SMILES for NP0292836 (6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol)

INCHI for NP0292836 (6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol)

Structure for NP0292836 (6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol)

3D Structure for NP0292836 (6-bromo-2-(3-hydroxy-3-{1,8,13,13-tetramethyl-2,7,12-trioxatricyclo[9.5.0.0³,⁸]hexadec-14-en-6-yl}butyl)-3,7,7-trimethyloxepan-3-ol)