NP-MRD: Showing NP-Card for 2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol (NP0168892)

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Record Information

Version

2.0

Created at

2022-09-03 04:45:45 UTC

Updated at

2022-09-03 04:45:45 UTC

NP-MRD ID

NP0168892

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol

Description

2,15-Dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]Triaconta-1(26),3(30),4,6,10(29),11,13,16(21),17,19,24,27-dodecaene-4,5,8,17-tetrol 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. 2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol is found in Marchantia paleacea and Marchantia polymorpha. 2,15-Dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]Triaconta-1(26),3(30),4,6,10(29),11,13,16(21),17,19,24,27-dodecaene-4,5,8,17-tetrol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251516172D          

 34 38  0  0  0  0            999 V2000
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    2.4923   -0.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167    0.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9840    0.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7857   -0.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3350   -1.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1327   -1.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4216   -0.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1806   -0.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4855   -1.6413    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


  Mrv1533004251516172D          

 34 38  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0168892

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2=CC=CC(OC3=C(O)C=CC=C3CCC3=CC=C(OC4=CC1=CC(O)=C4O)C=C3)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C28H24O6/c29-23-6-2-4-19-10-7-17-8-11-21(12-9-17)33-26-16-20(15-25(31)27(26)32)24(30)14-18-3-1-5-22(13-18)34-28(19)23/h1-6,8-9,11-13,15-16,24,29-32H,7,10,14H2

> <INCHI_KEY>
NJNMMLUSUMUVMX-UHFFFAOYSA-N

> <FORMULA>
C28H24O6

> <MOLECULAR_WEIGHT>
456.494

> <EXACT_MASS>
456.157288493

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
47.850721420310244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3(30),4,6,10,12,14(29),16,18,20,24,27-dodecaene-4,5,8,17-tetrol

> <ALOGPS_LOGP>
4.84

> <JCHEM_LOGP>
5.9317927180000005

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.851532371093935

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.24786523535817

> <JCHEM_PKA_STRONGEST_BASIC>
-3.130653052365658

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
128.6162

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3(30),4,6,10,12,14(29),16,18,20,24,27-dodecaene-4,5,8,17-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0       3.443  -0.066   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.652  -1.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.818   0.083   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.437   0.042   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.067  -1.469   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.092  -2.607   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.581  -2.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.120  -0.771   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.537  -1.568   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.106  -3.064   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.408  -2.241   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.346  -0.702   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.772  -2.957   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.833  -4.495   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.532  -5.318   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.168  -4.602   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.713  -6.205   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.725  -7.472   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.214  -8.015   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.144  -9.178   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.603  -8.862   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.047  -7.392   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.794  -6.408   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.734  -5.204   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.514  -3.842   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.849  -2.414   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.286  -2.413   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.433  -3.715   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.105  -3.647   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.169  -5.089   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.329  -6.380   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.125  -6.269   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.644  -6.569   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.000   0.356   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   34                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   33                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25    2   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   24   31                                                  
CONECT   31   30                                                            
CONECT   32   22   33                                                       
CONECT   33   32   19                                                       
CONECT   34    8    4                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₄O₆

Average Mass

456.4940 Da

Monoisotopic Mass

456.15729 Da

IUPAC Name

2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3(30),4,6,10,12,14(29),16,18,20,24,27-dodecaene-4,5,8,17-tetrol

Traditional Name

2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3(30),4,6,10,12,14(29),16,18,20,24,27-dodecaene-4,5,8,17-tetrol

CAS Registry Number

Not Available

SMILES

OC1CC2=CC=CC(OC3=C(O)C=CC=C3CCC3=CC=C(OC4=CC1=CC(O)=C4O)C=C3)=C2

InChI Identifier

InChI=1S/C28H24O6/c29-23-6-2-4-19-10-7-17-8-11-21(12-9-17)33-26-16-20(15-25(31)27(26)32)24(30)14-18-3-1-5-22(13-18)34-28(19)23/h1-6,8-9,11-13,15-16,24,29-32H,7,10,14H2

InChI Key

NJNMMLUSUMUVMX-UHFFFAOYSA-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
Marchantia paleacea	LOTUS Database	35616633
Marchantia polymorpha	LOTUS Database	35616633

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

Oxyneolignan skeleton
Diaryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.84	ALOGPS
logP	5.93	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	8.25	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	128.62 m³·mol⁻¹	ChemAxon
Polarizability	47.85 Å³	ChemAxon
Number of Rings	5	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

5319273

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol (NP0168892)

MOL for NP0168892 (2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol)

3D MOL for NP0168892 (2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol)

3D SDF for NP0168892 (2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol)

3D-SDF for NP0168892 (2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol)

PDB for NP0168892 (2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol)

3D PDB for NP0168892 (2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol)

SMILES for NP0168892 (2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol)

INCHI for NP0168892 (2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol)

Structure for NP0168892 (2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol)

3D Structure for NP0168892 (2,15-dioxapentacyclo[22.2.2.1³,⁷.1¹⁰,¹⁴.0¹⁶,²¹]triaconta-1(26),3,5,7(30),10(29),11,13,16,18,20,24,27-dodecaene-4,5,8,17-tetrol)