NP-MRD: Showing NP-Card for (-)-Macrophyllidimer B (NP0080702)

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Record Information

Version

2.0

Created at

2022-04-29 01:42:11 UTC

Updated at

2022-04-29 01:42:11 UTC

NP-MRD ID

NP0080702

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Macrophyllidimer B

Description

Macrophyllidimer B belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (-)-Macrophyllidimer B is found in Inula macrophylla. Based on a literature review very few articles have been published on Macrophyllidimer B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203422D          

 34 37  0  0  1  0            999 V2000
   -4.7686   -5.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9561   -4.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6739   -4.1861    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6739   -3.3611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3884   -2.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3884   -2.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1029   -3.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -2.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2450   -3.3611    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2450   -4.1861    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9594   -4.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4864   -4.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  3 34  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292203422D          

 34 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0080702

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1C[C@H]2[C@@H](C[C@@]1(C)C=C)OC(=O)[C@H]2CCC1=C2C[C@H](C(C)=C)[C@](C)(C[C@H]2OC1=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O4/c1-9-29(7)15-25-21(13-23(29)17(3)4)19(27(31)33-25)11-12-20-22-14-24(18(5)6)30(8,10-2)16-26(22)34-28(20)32/h9-10,19,21,23-26H,1-3,5,11-16H2,4,6-8H3/t19-,21+,23-,24+,25+,26+,29+,30-/m0/s1

> <INCHI_KEY>
YSSIFGYDZGBFIH-FEHALOKCSA-N

> <FORMULA>
C30H40O4

> <MOLECULAR_WEIGHT>
464.646

> <EXACT_MASS>
464.292659768

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.57816217819483

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,6R,7aR)-3-{2-[(3S,3aR,5S,6S,7aR)-6-ethenyl-6-methyl-2-oxo-5-(prop-1-en-2-yl)-octahydro-1-benzofuran-3-yl]ethyl}-6-ethenyl-6-methyl-5-(prop-1-en-2-yl)-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

> <ALOGPS_LOGP>
5.02

> <JCHEM_LOGP>
6.4064081046666645

> <ALOGPS_LOGS>
-5.80

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.248020633511693

> <JCHEM_PKA_STRONGEST_BASIC>
-6.677450631732741

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
135.2107

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.33e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6R,7aR)-3-{2-[(3S,3aR,5S,6S,7aR)-6-ethenyl-6-methyl-2-oxo-5-(prop-1-en-2-yl)-hexahydro-1-benzofuran-3-yl]ethyl}-6-ethenyl-6-methyl-5-(prop-1-en-2-yl)-4,5,7,7a-tetrahydro-1-benzofuran-2-one

> <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      -8.901  -9.529   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.385  -9.261   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.858  -7.814   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.858  -6.274   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.192  -5.504   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.192  -3.964   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.525  -6.274   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.524  -5.504   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.191  -6.274   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.191  -7.814   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.524  -8.584   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.726  -8.290   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.821  -7.044   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.281  -7.044   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.726  -5.798   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.250  -4.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.268  -0.057   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.531  -2.073   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.680   0.773   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.957   2.133   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.403  -0.479   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -8.375  -7.547   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11   34                                             
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    3                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   18   23                                                  
CONECT   23   22                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26   31   33                                             
CONECT   26   25   27   28                                                  
CONECT   27   26   19                                                       
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   25   32                                                       
CONECT   32   31                                                            
CONECT   33   25                                                            
CONECT   34    3                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₄

Average Mass

464.6460 Da

Monoisotopic Mass

464.29266 Da

IUPAC Name

(5R,6R,7aR)-3-{2-[(3S,3aR,5S,6S,7aR)-6-ethenyl-6-methyl-2-oxo-5-(prop-1-en-2-yl)-octahydro-1-benzofuran-3-yl]ethyl}-6-ethenyl-6-methyl-5-(prop-1-en-2-yl)-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

Traditional Name

(5R,6R,7aR)-3-{2-[(3S,3aR,5S,6S,7aR)-6-ethenyl-6-methyl-2-oxo-5-(prop-1-en-2-yl)-hexahydro-1-benzofuran-3-yl]ethyl}-6-ethenyl-6-methyl-5-(prop-1-en-2-yl)-4,5,7,7a-tetrahydro-1-benzofuran-2-one

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1C[C@H]2[C@@H](C[C@@]1(C)C=C)OC(=O)[C@H]2CCC1=C2C[C@H](C(C)=C)[C@](C)(C[C@H]2OC1=O)C=C

InChI Identifier

InChI=1S/C30H40O4/c1-9-29(7)15-25-21(13-23(29)17(3)4)19(27(31)33-25)11-12-20-22-14-24(18(5)6)30(8,10-2)16-26(22)34-28(20)32/h9-10,19,21,23-26H,1-3,5,11-16H2,4,6-8H3/t19-,21+,23-,24+,25+,26+,29+,30-/m0/s1

InChI Key

YSSIFGYDZGBFIH-FEHALOKCSA-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
Inula macrophylla	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Elemane sesquiterpenoid
Sesquiterpenoid
Benzofuran
2-furanone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
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	5.02	ALOGPS
logP	6.41	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	13.25	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	135.21 m³·mol⁻¹	ChemAxon
Polarizability	52.58 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

C00046109

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

101014001

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Macrophyllidimer B (NP0080702)

MOL for NP0080702 ((-)-Macrophyllidimer B)

3D MOL for NP0080702 ((-)-Macrophyllidimer B)

3D SDF for NP0080702 ((-)-Macrophyllidimer B)

3D-SDF for NP0080702 ((-)-Macrophyllidimer B)

PDB for NP0080702 ((-)-Macrophyllidimer B)

3D PDB for NP0080702 ((-)-Macrophyllidimer B)

SMILES for NP0080702 ((-)-Macrophyllidimer B)

INCHI for NP0080702 ((-)-Macrophyllidimer B)

Structure for NP0080702 ((-)-Macrophyllidimer B)

3D Structure for NP0080702 ((-)-Macrophyllidimer B)