NP-MRD: Showing NP-Card for (1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate (NP0317462)

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Record Information

Version

2.0

Created at

2022-09-11 17:22:02 UTC

Updated at

2022-09-11 17:22:02 UTC

NP-MRD ID

NP0317462

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate

Description

Briarellin a belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. (1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate is found in Briareum asbestinum. Based on a literature review very few articles have been published on briarellin a.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112219222D          

 35 38  0  0  1  0            999 V2000
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   -3.6536   -0.8168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6735   -1.6018    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9880   -2.0817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1952   -2.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309112219222D          

 35 38  0  0  1  0            999 V2000
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    2.4332    0.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1477    1.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9196    1.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7548    1.1951    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0562    1.9631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  1  0  0  0
 11 14  1  0  0  0  0
 14  4  1  1  0  0  0
  7 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 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  1  0  0  0  0
 22 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0317462

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)O[C@@H]1C[C@H](O)C(=C)C[C@@H]2O[C@H]3[C@@H]4[C@H]2[C@](C)(O)CC[C@H]4[C@@H](C)C(=O)O[C@@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O7/c1-6-7-8-9-10-11-22(30)34-21-15-19(29)16(2)14-20-24-23-18(12-13-27(24,4)32)17(3)26(31)35-28(21,5)25(23)33-20/h17-21,23-25,29,32H,2,6-15H2,1,3-5H3/t17-,18+,19+,20+,21-,23+,24+,25+,27-,28+/m1/s1

> <INCHI_KEY>
BSGHPVXUHAMISR-HMIFWFFKSA-N

> <FORMULA>
C28H44O7

> <MOLECULAR_WEIGHT>
492.653

> <EXACT_MASS>
492.308703757

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.18864115647645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3R,4R,7R,8R,11S,12R,14S,17S)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0^{2,7}.0^{3,17}]octadecan-12-yl octanoate

> <JCHEM_LOGP>
3.6745707649999986

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.92425634210533

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.308399715513517

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9326748798415565

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
130.23069999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,4R,7R,8R,11S,12R,14S,17S)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0^{2,7}.0^{3,17}]octadecan-12-yl octanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0     -11.438   1.853   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.067   1.152   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.247  -0.486   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.472  -1.971   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -8.329  -1.530   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -6.820  -1.525   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.857  -2.990   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.578  -3.886   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.964  -5.414   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.433  -5.931   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.618  -4.911   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.369  -6.256   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -10.085  -4.444   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -8.454  -3.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.040  -3.367   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.987  -4.490   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.449  -1.924   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.914  -1.801   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.257  -0.603   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.827  -0.330   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.749   0.769   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.127   1.216   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.794   1.986   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.460   1.216   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.460  -0.324   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.126   1.986   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.793   1.216   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.541   1.986   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.875   1.216   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.208   1.986   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.542   1.216   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.876   1.986   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -7.317   2.249   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -8.876   2.231   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -9.438   3.665   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11    4    7                                                  
CONECT   15    8   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    6   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   33                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   22   34                                                       
CONECT   34   33    2   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₄O₇

Average Mass

492.6530 Da

Monoisotopic Mass

492.30870 Da

IUPAC Name

(1S,2S,3R,4R,7R,8R,11S,12R,14S,17S)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0^{2,7}.0^{3,17}]octadecan-12-yl octanoate

Traditional Name

(1S,2S,3R,4R,7R,8R,11S,12R,14S,17S)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0^{2,7}.0^{3,17}]octadecan-12-yl octanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)O[C@@H]1C[C@H](O)C(=C)C[C@@H]2O[C@H]3[C@@H]4[C@H]2[C@](C)(O)CC[C@H]4[C@@H](C)C(=O)O[C@@]13C

InChI Identifier

InChI=1S/C28H44O7/c1-6-7-8-9-10-11-22(30)34-21-15-19(29)16(2)14-20-24-23-18(12-13-27(24,4)32)17(3)26(31)35-28(21,5)25(23)33-20/h17-21,23-25,29,32H,2,6-15H2,1,3-5H3/t17-,18+,19+,20+,21-,23+,24+,25+,27-,28+/m1/s1

InChI Key

BSGHPVXUHAMISR-HMIFWFFKSA-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
Briareum asbestinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Not Available

Direct Parent

Lactones

Alternative Parents

Substituents

Caprolactone
Fatty acid ester
Oxepane
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
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	3.67	ChemAxon
pKa (Strongest Acidic)	14.31	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.23 m³·mol⁻¹	ChemAxon
Polarizability	55.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

8158728

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9983138

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate (NP0317462)

MOL for NP0317462 ((1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate)

3D MOL for NP0317462 ((1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate)

3D SDF for NP0317462 ((1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate)

3D-SDF for NP0317462 ((1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate)

PDB for NP0317462 ((1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate)

3D PDB for NP0317462 ((1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate)

SMILES for NP0317462 ((1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate)

INCHI for NP0317462 ((1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate)

Structure for NP0317462 ((1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate)

3D Structure for NP0317462 ((1s,2s,3r,4r,7r,8r,11s,12r,14s,17s)-4,14-dihydroxy-4,8,11-trimethyl-15-methylidene-9-oxo-10,18-dioxatetracyclo[9.7.0.0²,⁷.0³,¹⁷]octadecan-12-yl octanoate)