NP-MRD: Showing NP-Card for (-)-Briaranolide H (NP0078354)

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Record Information

Version

2.0

Created at

2022-04-28 23:27:04 UTC

Updated at

2022-04-28 23:27:04 UTC

NP-MRD ID

NP0078354

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Briaranolide H

Description

Briaranolide H belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (-)-Briaranolide H is found in Briareum sp. Based on a literature review very few articles have been published on Briaranolide H.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201272D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292201272D          

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    2.4617   -0.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0822    0.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -0.8124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496   -0.4888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4855    0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5351   -3.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7266   -3.5499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9941   -3.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2991   -3.4847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9565   -4.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2239   -5.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1863   -5.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -2.7909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1541   -3.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215   -3.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8490   -4.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8114   -4.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2293   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1821    0.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  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
  3 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 16 26  1  6  0  0  0
 23 27  1  0  0  0  0
 17 27  1  6  0  0  0
 23 28  1  1  0  0  0
 14 29  1  0  0  0  0
 12 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 11 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
  4 41  1  1  0  0  0
  2 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078354

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)O[C@H]1C\C(C)=C/[C@@H]2OC(=O)[C@]3(C)O[C@]23[C@@H](OC(C)=O)[C@H]2C(C)=CC[C@H](OC(C)=O)[C@]2(C)[C@H]1OC(=O)CC

> <INCHI_IDENTIFIER>
InChI=1S/C31H42O11/c1-9-11-24(35)39-20-14-16(3)15-22-31(30(8,42-31)28(36)40-22)27(38-19(6)33)25-17(4)12-13-21(37-18(5)32)29(25,7)26(20)41-23(34)10-2/h12,15,20-22,25-27H,9-11,13-14H2,1-8H3/b16-15-/t20-,21-,22-,25+,26-,27-,29-,30-,31-/m0/s1

> <INCHI_KEY>
IKFPLXHSMAIESM-IGUOHBOOSA-N

> <FORMULA>
C31H42O11

> <MOLECULAR_WEIGHT>
590.666

> <EXACT_MASS>
590.272712172

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
61.02064074595351

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3S,7S,8R,9R,10S,12Z,14S,17R)-2,7-bis(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-9-(propanoyloxy)-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-4,12-dien-10-yl butanoate

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.4615612089999988

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.360429649274516

> <JCHEM_POLAR_SURFACE_AREA>
144.03000000000003

> <JCHEM_REFRACTIVITY>
146.5169

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3S,7S,8R,9R,10S,12Z,14S,17R)-2,7-bis(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-9-(propanoyloxy)-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-4,12-dien-10-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      10.471   0.236   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.104  -0.473   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.034  -2.011   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.331  -2.841   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.698  -2.133   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.768  -0.594   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.995  -2.963   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.363  -2.254   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.433  -0.716   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      15.660  -3.084   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.261  -4.380   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.893  -5.088   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.596  -4.258   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.229  -4.966   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.931  -4.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.002  -2.598   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.369  -1.890   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.666  -2.720   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.208  -1.278   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.231  -0.088   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.773   1.353   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.565  -0.178   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.118  -0.370   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.595  -0.140   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.887   1.228   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.905  -1.516   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       7.559  -0.912   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.506   1.120   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.599  -6.987   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.823  -6.626   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.456  -7.335   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.158  -6.505   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.385  -8.873   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.018  -9.582   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.948 -11.120   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.558  -5.210   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      11.488  -6.748   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      10.120  -7.456   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      12.785  -7.578   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.715  -9.116   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.628  -3.671   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.807   0.357   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   42                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5   11   41                                             
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4   12   36                                                  
CONECT   12   11   13   30                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   26                                                  
CONECT   17   16   18   23   27                                             
CONECT   18   17    3   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24   27   28                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   16                                                       
CONECT   27   23   17                                                       
CONECT   28   23                                                            
CONECT   29   14                                                            
CONECT   30   12   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   11   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39                                                            
CONECT   41    4                                                            
CONECT   42    2                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₂O₁₁

Average Mass

590.6660 Da

Monoisotopic Mass

590.27271 Da

IUPAC Name

(1S,2S,3S,7S,8R,9R,10S,12Z,14S,17R)-2,7-bis(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-9-(propanoyloxy)-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-4,12-dien-10-yl butanoate

Traditional Name

(1S,2S,3S,7S,8R,9R,10S,12Z,14S,17R)-2,7-bis(acetyloxy)-4,8,12,17-tetramethyl-16-oxo-9-(propanoyloxy)-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-4,12-dien-10-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@H]1C\C(C)=C/[C@@H]2OC(=O)[C@]3(C)O[C@]23[C@@H](OC(C)=O)[C@H]2C(C)=CC[C@H](OC(C)=O)[C@]2(C)[C@H]1OC(=O)CC

InChI Identifier

InChI=1S/C31H42O11/c1-9-11-24(35)39-20-14-16(3)15-22-31(30(8,42-31)28(36)40-22)27(38-19(6)33)25-17(4)12-13-21(37-18(5)32)29(25,7)26(20)41-23(34)10-2/h12,15,20-22,25-27H,9-11,13-14H2,1-8H3/b16-15-/t20-,21-,22-,25+,26-,27-,29-,30-,31-/m0/s1

InChI Key

IKFPLXHSMAIESM-IGUOHBOOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 sp.	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Briarane diterpenoid
Pentacarboxylic acid or derivatives
Fatty acid ester
Para-dioxane
Gamma butyrolactone
Fatty acyl
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	3.41	ALOGPS
logP	3.46	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	144.03 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	146.52 m³·mol⁻¹	ChemAxon
Polarizability	61.02 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

C00042310

Chemspider ID

9723607

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11548828

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Briaranolide H (NP0078354)

MOL for NP0078354 ((-)-Briaranolide H)

3D MOL for NP0078354 ((-)-Briaranolide H)

3D SDF for NP0078354 ((-)-Briaranolide H)

3D-SDF for NP0078354 ((-)-Briaranolide H)

PDB for NP0078354 ((-)-Briaranolide H)

3D PDB for NP0078354 ((-)-Briaranolide H)

SMILES for NP0078354 ((-)-Briaranolide H)

INCHI for NP0078354 ((-)-Briaranolide H)

Structure for NP0078354 ((-)-Briaranolide H)

3D Structure for NP0078354 ((-)-Briaranolide H)