NP-MRD: Showing NP-Card for (-)-Mastigophorene B (NP0072228)

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Record Information

Version

2.0

Created at

2022-04-28 17:35:42 UTC

Updated at

2022-04-28 17:35:42 UTC

NP-MRD ID

NP0072228

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Mastigophorene B

Description

Mastigophorene a belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Thus, mastigophorene a is considered to be an isoprenoid. (-)-Mastigophorene B is found in Herbertus dicranus, Herbertus sakuraii, Mastigophora diclados and Mastigophora diclados (BRID.) NEES. (-)-Mastigophorene B was first documented in 2010 (PMID: 20458547). Based on a literature review very few articles have been published on Mastigophorene a (PMID: 26878822).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304282219352D          

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M  END

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M  END

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 16 21  1  0  0  0  0
 15 22  1  1  0  0  0
 10 23  1  0  0  0  0
  9 24  1  0  0  0  0
  3 25  1  0  0  0  0
  2 26  1  0  0  0  0
 27  1  1  1  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
 27 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 27 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0072228

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=C(O)C(O)=C1C1=C(O)C(O)=C(C=C1C)[C@@]1(C)CCCC1(C)C)[C@@]1(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O4/c1-17-15-19(29(7)13-9-11-27(29,3)4)23(31)25(33)21(17)22-18(2)16-20(24(32)26(22)34)30(8)14-10-12-28(30,5)6/h15-16,31-34H,9-14H2,1-8H3/t29-,30-/m1/s1

> <INCHI_KEY>
TZWQPPFRZCEUCT-LOYHVIPDSA-N

> <FORMULA>
C30H42O4

> <MOLECULAR_WEIGHT>
466.662

> <EXACT_MASS>
466.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.12206998209156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,6'-dimethyl-4,4'-bis[(1S)-1,2,2-trimethylcyclopentyl]-[1,1'-biphenyl]-2,2',3,3'-tetrol

> <ALOGPS_LOGP>
6.52

> <JCHEM_LOGP>
8.548120498666666

> <ALOGPS_LOGS>
-5.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.826465533891456

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.008932633121486

> <JCHEM_PKA_STRONGEST_BASIC>
-5.826951116786854

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
139.37900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,6'-dimethyl-4,4'-bis[(1S)-1,2,2-trimethylcyclopentyl]-[1,1'-biphenyl]-2,2',3,3'-tetrol

> <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      -3.973  13.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.448  11.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.418  10.391   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.912  10.711   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.436  12.176   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.466  13.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.071  12.496   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.881   9.567   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.625   9.887   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.656   8.743   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.180   7.278   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.327   6.958   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.357   8.102   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.863   7.782   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.210   6.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.456   5.228   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.980   3.764   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.440   3.764   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.964   5.228   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.966   4.924   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.499   6.362   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.241   7.278   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.162   9.063   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.101  11.352   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.894   8.926   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -5.955  11.215   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.003  14.145   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.249  15.050   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.773  16.514   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.233  16.514   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.757  15.050   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.247  15.354   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.715  13.916   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -6.033  13.000   0.000  0.00  0.00           C+0
CONECT    1    2    6   27                                                  
CONECT    2    1    3   26                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    4    9   13                                                  
CONECT    9    8   10   24                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   11   16   19   22                                             
CONECT   16   15   17   20   21                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20   16                                                            
CONECT   21   16                                                            
CONECT   22   15                                                            
CONECT   23   10                                                            
CONECT   24    9                                                            
CONECT   25    3                                                            
CONECT   26    2                                                            
CONECT   27    1   28   31   34                                             
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   27   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   27                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Mastigophorene b	MeSH

Chemical Formula

C₃₀H₄₂O₄

Average Mass

466.6620 Da

Monoisotopic Mass

466.30831 Da

IUPAC Name

6,6'-dimethyl-4,4'-bis[(1S)-1,2,2-trimethylcyclopentyl]-[1,1'-biphenyl]-2,2',3,3'-tetrol

Traditional Name

6,6'-dimethyl-4,4'-bis[(1S)-1,2,2-trimethylcyclopentyl]-[1,1'-biphenyl]-2,2',3,3'-tetrol

CAS Registry Number

Not Available

SMILES

CC1=CC(=C(O)C(O)=C1C1=C(O)C(O)=C(C=C1C)[C@@]1(C)CCCC1(C)C)[C@@]1(C)CCCC1(C)C

InChI Identifier

InChI=1S/C30H42O4/c1-17-15-19(29(7)13-9-11-27(29,3)4)23(31)25(33)21(17)22-18(2)16-20(24(32)26(22)34)30(8)14-10-12-28(30,5)6/h15-16,31-34H,9-14H2,1-8H3/t29-,30-/m1/s1

InChI Key

TZWQPPFRZCEUCT-LOYHVIPDSA-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
Herbertus dicranus	LOTUS Database	35616633
Herbertus sakuraii	Plant	KNApSAcK
Mastigophora diclados	LOTUS Database	35616633
Mastigophora diclados (BRID.) NEES	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Neolignan skeleton
Herbertane sesquiterpenoid
Cuparane sesquiterpenoid
Sesquiterpenoid
Biphenol
Biphenyl
Catechol
M-cresol
P-cresol
1-hydroxy-4-unsubstituted benzenoid
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	6.52	ALOGPS
logP	8.55	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	9.01	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	139.38 m³·mol⁻¹	ChemAxon
Polarizability	55.12 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00032002

Chemspider ID

8610138

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10434712

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Komala I, Ito T, Nagashima F, Yagi Y, Asakawa Y: Cytotoxic, radical scavenging and antimicrobial activities of sesquiterpenoids from the Tahitian liverwort Mastigophora diclados (Brid.) Nees (Mastigophoraceae). J Nat Med. 2010 Oct;64(4):417-22. doi: 10.1007/s11418-010-0423-8. Epub 2010 May 12. [PubMed:20458547 ]
Buter J, Heijnen D, Vila C, Hornillos V, Otten E, Giannerini M, Minnaard AJ, Feringa BL: Palladium-Catalyzed, tert-Butyllithium-Mediated Dimerization of Aryl Halides and Its Application in the Atropselective Total Synthesis of Mastigophorene A. Angew Chem Int Ed Engl. 2016 Mar 7;55(11):3620-4. doi: 10.1002/anie.201510328. Epub 2016 Feb 16. [PubMed:26878822 ]

Showing NP-Card for (-)-Mastigophorene B (NP0072228)

MOL for NP0072228 ((-)-Mastigophorene B)

3D MOL for NP0072228 ((-)-Mastigophorene B)

3D SDF for NP0072228 ((-)-Mastigophorene B)

3D-SDF for NP0072228 ((-)-Mastigophorene B)

PDB for NP0072228 ((-)-Mastigophorene B)

3D PDB for NP0072228 ((-)-Mastigophorene B)

SMILES for NP0072228 ((-)-Mastigophorene B)

INCHI for NP0072228 ((-)-Mastigophorene B)

Structure for NP0072228 ((-)-Mastigophorene B)

3D Structure for NP0072228 ((-)-Mastigophorene B)