NP-MRD: Showing NP-Card for illicidione b (NP0232077)

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Record Information

Version

2.0

Created at

2022-09-06 13:11:33 UTC

Updated at

2022-09-06 13:11:33 UTC

NP-MRD ID

NP0232077

Secondary Accession Numbers

None

Natural Product Identification

Common Name

illicidione b

Description

Illicidione B belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. illicidione b is found in Illicium oligandrum. Based on a literature review very few articles have been published on Illicidione B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062215112D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062215112D          

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 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 30 34  1  0  0  0  0
 18 34  1  0  0  0  0
 34 35  2  0  0  0  0
 16 36  1  0  0  0  0
  4 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0232077

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@H]1C[C@@]2(O)C=C(CC=C)C(=O)C(CC3=C4O[C@H](C[C@@]4(O)C=C(CC=C)C3=O)C(C)(C)O)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O8/c1-7-9-16-12-28(34)14-20(26(3,4)32)36-24(28)18(22(16)30)11-19-23(31)17(10-8-2)13-29(35)15-21(27(5,6)33)37-25(19)29/h7-8,12-13,20-21,32-35H,1-2,9-11,14-15H2,3-6H3/t20-,21-,28+,29+/m1/s1

> <INCHI_KEY>
AVMQANMZZMKFSS-SKZNYKRCSA-N

> <FORMULA>
C29H36O8

> <MOLECULAR_WEIGHT>
512.599

> <EXACT_MASS>
512.241018119

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.39241097955031

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3aR)-7-{[(2R,3aR)-3a-hydroxy-2-(2-hydroxypropan-2-yl)-6-oxo-5-(prop-2-en-1-yl)-2,3,3a,6-tetrahydro-1-benzofuran-7-yl]methyl}-3a-hydroxy-2-(2-hydroxypropan-2-yl)-5-(prop-2-en-1-yl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one

> <JCHEM_LOGP>
1.3040828523333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.150039377271227

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.540974448020393

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1039337328930205

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
142.0064

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3aR)-7-{[(2R,3aR)-3a-hydroxy-2-(2-hydroxypropan-2-yl)-6-oxo-5-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-3a-hydroxy-2-(2-hydroxypropan-2-yl)-5-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.247  -6.295   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.681  -6.896   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.149  -7.057   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.379  -8.391   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.609  -9.725   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.046  -7.621   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.713  -9.161   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.523  -5.650   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.910   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.450   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.910   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.910  -0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.465   2.016   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.161   3.072   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.906  -1.064   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   36                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    9   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15   17   36                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   34                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   21   27                                                       
CONECT   27   26   19   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   30   18   35                                                  
CONECT   35   34                                                            
CONECT   36   16    4   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₈

Average Mass

512.5990 Da

Monoisotopic Mass

512.24102 Da

IUPAC Name

(2R,3aR)-7-{[(2R,3aR)-3a-hydroxy-2-(2-hydroxypropan-2-yl)-6-oxo-5-(prop-2-en-1-yl)-2,3,3a,6-tetrahydro-1-benzofuran-7-yl]methyl}-3a-hydroxy-2-(2-hydroxypropan-2-yl)-5-(prop-2-en-1-yl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one

Traditional Name

(2R,3aR)-7-{[(2R,3aR)-3a-hydroxy-2-(2-hydroxypropan-2-yl)-6-oxo-5-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-7-yl]methyl}-3a-hydroxy-2-(2-hydroxypropan-2-yl)-5-(prop-2-en-1-yl)-2,3-dihydro-1-benzofuran-6-one

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@H]1C[C@@]2(O)C=C(CC=C)C(=O)C(CC3=C4O[C@H](C[C@@]4(O)C=C(CC=C)C3=O)C(C)(C)O)=C2O1

InChI Identifier

InChI=1S/C29H36O8/c1-7-9-16-12-28(34)14-20(26(3,4)32)36-24(28)18(22(16)30)11-19-23(31)17(10-8-2)13-29(35)15-21(27(5,6)33)37-25(19)29/h7-8,12-13,20-21,32-35H,1-2,9-11,14-15H2,3-6H3/t20-,21-,28+,29+/m1/s1

InChI Key

AVMQANMZZMKFSS-SKZNYKRCSA-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
Illicium oligandrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Vinylogous ester
Tetrahydrofuran
Tertiary alcohol
Cyclic ketone
Ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

disaccharide (CHEBI:67761 )

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	1.3	ChemAxon
pKa (Strongest Acidic)	12.54	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	142.01 m³·mol⁻¹	ChemAxon
Polarizability	53.39 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	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

26341636

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53262722

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for illicidione b (NP0232077)

MOL for NP0232077 (illicidione b)

3D MOL for NP0232077 (illicidione b)

3D SDF for NP0232077 (illicidione b)

3D-SDF for NP0232077 (illicidione b)

PDB for NP0232077 (illicidione b)

3D PDB for NP0232077 (illicidione b)

SMILES for NP0232077 (illicidione b)

INCHI for NP0232077 (illicidione b)

Structure for NP0232077 (illicidione b)

3D Structure for NP0232077 (illicidione b)