NP-MRD: Showing NP-Card for (1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one (NP0272919)

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Record Information

Version

2.0

Created at

2022-09-08 19:45:50 UTC

Updated at

2022-09-08 19:45:50 UTC

NP-MRD ID

NP0272919

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one

Description

Tonkinensine A belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. (1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one is found in Sophora tonkinensis. Based on a literature review very few articles have been published on Tonkinensine A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082221452D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309082221452D          

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 30 31  1  0  0  0  0
 32 31  1  1  0  0  0
 17 32  1  0  0  0  0
 24 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 27 35  1  0  0  0  0
 13 36  1  0  0  0  0
  9 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272919

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1CN1C[C@@H]3C[C@H](C1)C1=CC=CC(=O)N1C3)[C@@H]1OC3=CC4=C(OCO4)C=C3[C@@H]1CO2

> <INCHI_IDENTIFIER>
InChI=1S/C28H26N2O6/c31-22-7-23-19(28-20(13-33-23)18-6-25-26(35-14-34-25)8-24(18)36-28)5-17(22)12-29-9-15-4-16(11-29)21-2-1-3-27(32)30(21)10-15/h1-3,5-8,15-16,20,28,31H,4,9-14H2/t15-,16+,20-,28-/m0/s1

> <INCHI_KEY>
LQAUBEXTCPPEEH-AIQFOMFISA-N

> <FORMULA>
C28H26N2O6

> <MOLECULAR_WEIGHT>
486.524

> <EXACT_MASS>
486.179086565

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
51.26197697138073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,9S)-11-{[(1R,12R)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one

> <JCHEM_LOGP>
1.2066624415574942

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.503595857841942

> <JCHEM_PKA_STRONGEST_BASIC>
8.166244587180806

> <JCHEM_POLAR_SURFACE_AREA>
80.70000000000002

> <JCHEM_REFRACTIVITY>
133.14239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9S)-11-{[(1R,12R)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0      -5.058  -8.891   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.371  -7.512   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.222  -6.228   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.535  -4.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.998  -4.756   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.147  -6.040   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.834  -7.418   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -2.345  -8.878   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.967  -9.565   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.329  -7.523   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.687  -5.551   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.691  -6.237   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.180  -7.698   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.716  -7.805   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.577  -6.528   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.114  -6.635   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.974  -5.358   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.299  -3.974   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.763  -3.867   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.902  -5.144   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.366  -5.037   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.160  -2.697   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.696  -2.804   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.372  -4.188   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.852  -4.612   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.158  -3.796   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.518  -4.519   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.572  -6.058   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.266  -6.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.906  -6.151   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.459  -6.679   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.511  -5.465   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      14.052  -6.482   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.913  -5.205   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.965  -3.992   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.493  -9.076   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   36                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   36                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   32                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20                                                            
CONECT   22   18   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   35                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   17   24                                                  
CONECT   33   28   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   27                                                       
CONECT   36   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₆N₂O₆

Average Mass

486.5240 Da

Monoisotopic Mass

486.17909 Da

IUPAC Name

(1R,9S)-11-{[(1R,12R)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one

Traditional Name

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C=C1CN1C[C@@H]3C[C@H](C1)C1=CC=CC(=O)N1C3)[C@@H]1OC3=CC4=C(OCO4)C=C3[C@@H]1CO2

InChI Identifier

InChI=1S/C28H26N2O6/c31-22-7-23-19(28-20(13-33-23)18-6-25-26(35-14-34-25)8-24(18)36-28)5-17(22)12-29-9-15-4-16(11-29)21-2-1-3-27(32)30(21)10-15/h1-3,5-8,15-16,20,28,31H,4,9-14H2/t15-,16+,20-,28-/m0/s1

InChI Key

LQAUBEXTCPPEEH-AIQFOMFISA-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
Sophora tonkinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
Cytisine
1-benzopyran
Chromane
Benzopyran
Benzodioxole
Alkaloid or derivatives
Benzofuran
Coumaran
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Pyridinone
Alkyl aryl ether
Benzenoid
Piperidine
Pyridine
Heteroaromatic compound
Lactam
Tertiary aliphatic amine
Tertiary amine
Acetal
Oxacycle
Ether
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
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	1.21	ChemAxon
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	8.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.14 m³·mol⁻¹	ChemAxon
Polarizability	51.26 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

24898927

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one (NP0272919)

MOL for NP0272919 ((1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D MOL for NP0272919 ((1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D SDF for NP0272919 ((1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D-SDF for NP0272919 ((1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

PDB for NP0272919 ((1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D PDB for NP0272919 ((1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

SMILES for NP0272919 ((1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

INCHI for NP0272919 ((1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

Structure for NP0272919 ((1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)

3D Structure for NP0272919 ((1r,9s)-11-{[(1r,12r)-16-hydroxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-15-yl]methyl}-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one)