NP-MRD: Showing NP-Card for Gochnatiolide B (NP0064054)

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Record Information

Version

2.0

Created at

2022-04-28 08:20:55 UTC

Updated at

2022-04-28 08:20:55 UTC

NP-MRD ID

NP0064054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gochnatiolide B

Description

(1'R,2'S,3aS,6'S,6aR,9R,9aR,9bS,13'S)-13'-hydroxy-3,5',6,15'-tetramethylidene-3,3a,4,5,6,6a,7,8,9a,9b-decahydro-2H-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]Hexadecan]-9'(16')-ene-2,4',8,14'-tetrone belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Gochnatiolide B is found in Gochnaria paniculata and Gochnatia paniculata. Based on a literature review very few articles have been published on (1'R,2'S,3aS,6'S,6aR,9R,9aR,9bS,13'S)-13'-hydroxy-3,5',6,15'-tetramethylidene-3,3a,4,5,6,6a,7,8,9a,9b-decahydro-2H-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]Hexadecan]-9'(16')-ene-2,4',8,14'-tetrone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282210202D          

 37 43  0  0  1  0            999 V2000
    5.0242    2.1199    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


  Mrv1652304282210202D          

 37 43  0  0  1  0            999 V2000
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 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 14 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 19  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 25 35  1  1  0  0  0
 35 36  2  0  0  0  0
 18 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0064054

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@]12C(=O)C(=C)[C@@H]3[C@H]4OC(=O)C(=C)[C@@H]4CCC(CC[C@@]11[C@@H]4[C@H]5OC(=O)C(=C)[C@@H]5CCC(=C)[C@@H]4CC1=O)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C30H30O7/c1-12-5-7-18-14(3)28(34)37-25(18)23-19(12)11-20(31)29(23)10-9-16-6-8-17-13(2)27(33)36-24(17)21-15(4)26(32)30(29,35)22(16)21/h17-19,21,23-25,35H,1-11H2/t17-,18-,19-,21-,23-,24-,25-,29+,30+/m0/s1

> <INCHI_KEY>
FJSHUGOPWDQYLC-SDIRPBJHSA-N

> <FORMULA>
C30H30O7

> <MOLECULAR_WEIGHT>
502.563

> <EXACT_MASS>
502.199153306

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.02807033408088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2'S,3aS,6'S,6aR,9R,9aR,9bS,13'S)-13'-hydroxy-3,5',6,15'-tetramethylidene-3,3a,4,5,6,6a,7,8,9a,9b-decahydro-2H-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadecan]-9'(16')-ene-2,4',8,14'-tetrone

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
3.496924628

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.358259578333886

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.947573721085076

> <JCHEM_PKA_STRONGEST_BASIC>
-4.133931235907954

> <JCHEM_POLAR_SURFACE_AREA>
106.97000000000001

> <JCHEM_REFRACTIVITY>
131.84680000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2'S,3aS,6'S,6aR,9R,9aR,9bS,13'S)-13'-hydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadecan]-9'(16')-ene-2,4',8,14'-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.379   3.957   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.284   5.040   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.009   6.474   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.754   4.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.942   3.551   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.458   2.101   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.915   1.600   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.214   2.426   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.888   0.060   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.119  -0.963   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.416  -0.391   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.188  -2.010   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.532   0.870   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.447   3.920   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.759   5.555   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.421   6.772   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.761   6.037   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.998   4.443   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.821   3.449   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.002   1.920   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.541   1.411   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.718   2.404   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.919   0.825   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.613   0.990   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.439   2.289   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.938   3.745   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.513   4.262   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.881   5.757   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.193   6.975   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.417   5.869   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.833   7.704   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.168   4.672   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -3.429   3.788   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.933   4.321   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.979   2.316   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.014   1.099   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.763   5.769   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   17                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    1                                                       
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6                                                       
CONECT   14    5   15   18   22                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    4                                                       
CONECT   18   14   19   30   37                                             
CONECT   19   18   20   27                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   14                                                       
CONECT   23   20   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   35                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   19   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   18   31                                                  
CONECT   31   30                                                            
CONECT   32   26   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   25   36                                                  
CONECT   36   35                                                            
CONECT   37   18                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₀O₇

Average Mass

502.5630 Da

Monoisotopic Mass

502.19915 Da

IUPAC Name

Traditional Name

(1'R,2'S,3aS,6'S,6aR,9R,9aR,9bS,13'S)-13'-hydroxy-3,5',6,15'-tetramethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-3'-oxaspiro[azuleno[4,5-b]furan-9,12'-tetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadecan]-9'(16')-ene-2,4',8,14'-tetrone

CAS Registry Number

Not Available

SMILES

O[C@]12C(=O)C(=C)[C@@H]3[C@H]4OC(=O)C(=C)[C@@H]4CCC(CC[C@@]11[C@@H]4[C@H]5OC(=O)C(=C)[C@@H]5CCC(=C)[C@@H]4CC1=O)=C23

InChI Identifier

InChI=1S/C30H30O7/c1-12-5-7-18-14(3)28(34)37-25(18)23-19(12)11-20(31)29(23)10-9-16-6-8-17-13(2)27(33)36-24(17)21-15(4)26(32)30(29,35)22(16)21/h17-19,21,23-25,35H,1-11H2/t17-,18-,19-,21-,23-,24-,25-,29+,30+/m0/s1

InChI Key

FJSHUGOPWDQYLC-SDIRPBJHSA-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
Gochnaria paniculata	-	KNApSAcK
Gochnatia paniculata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Guaianolide-skeleton
Terpene lactone
Guaiane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	1.33	ALOGPS
logP	3.5	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.95	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.97 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	131.85 m³·mol⁻¹	ChemAxon
Polarizability	53.03 Å³	ChemAxon
Number of Rings	7	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

162996499

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gochnatiolide B (NP0064054)

MOL for NP0064054 (Gochnatiolide B)

3D MOL for NP0064054 (Gochnatiolide B)

3D SDF for NP0064054 (Gochnatiolide B)

3D-SDF for NP0064054 (Gochnatiolide B)

PDB for NP0064054 (Gochnatiolide B)

3D PDB for NP0064054 (Gochnatiolide B)

SMILES for NP0064054 (Gochnatiolide B)

INCHI for NP0064054 (Gochnatiolide B)

Structure for NP0064054 (Gochnatiolide B)

3D Structure for NP0064054 (Gochnatiolide B)