NP-MRD: Showing NP-Card for Anhydropisatin (NP0045694)

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Record Information

Version

2.0

Created at

2022-03-17 19:35:55 UTC

Updated at

2022-03-17 19:35:55 UTC

NP-MRD ID

NP0045694

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Anhydropisatin

Description

Anhydropisatin is found in Derris laxiflora, Derris urucu, Flemingia chappar, Millettia pachyloba, Derris scandens , Sophora japonica , Tephrosia candida, Tephrosia purpurea and Tephrosia tinctoria.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212172D          

 22 26  0  0  0  0            999 V2000
   -4.7437    2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4582    1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4582    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7437    0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0293    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0293    1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148    2.1509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004    1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859    0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -0.3241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148    0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1714    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1714   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3276    0.7558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4570    0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4570   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3276   -0.5790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1727    2.1509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8872    1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  5  6  2  0  0  0  0
  5 13  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13  9  2  0  0  0  0
 11 15  2  0  0  0  0
 10 11  1  0  0  0  0
 14 10  2  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 19 18  2  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045694

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C1=C(CO2)C2=CC3=C(OCO3)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O5/c1-18-9-2-3-10-13(4-9)19-7-12-11-5-15-16(21-8-20-15)6-14(11)22-17(10)12/h2-6H,7-8H2,1H3

> <INCHI_KEY>
XWTCRKNSJARUIU-UHFFFAOYSA-N

> <FORMULA>
C17H12O5

> <MOLECULAR_WEIGHT>
296.2742

> <EXACT_MASS>
296.068473494

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.142641899006026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13(18),14,16-heptaene

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
2.75871394

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.162875529035055

> <JCHEM_POLAR_SURFACE_AREA>
50.06

> <JCHEM_REFRACTIVITY>
77.16069999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
anhydropisatin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -8.855   4.015   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.189   3.245   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.189   1.705   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.855   0.935   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.521   1.705   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.521   3.245   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.188   4.015   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.854   3.245   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.854   1.705   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.520   0.935   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.520  -0.605   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.188  -0.605   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -6.188   0.935   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.187   1.705   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.187  -1.375   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.517   0.165   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.612   1.411   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.853   0.935   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.853  -0.605   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.612  -1.081   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0     -11.522   4.015   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -12.856   3.245   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   14                                                  
CONECT   11   12   15   10                                                  
CONECT   12   11   13                                                       
CONECT   13    5   12    9                                                  
CONECT   14   10   18                                                       
CONECT   15   11   19                                                       
CONECT   16   17   20                                                       
CONECT   17   16   18                                                       
CONECT   18   14   17   19                                                  
CONECT   19   15   20   18                                                  
CONECT   20   16   19                                                       
CONECT   21    2   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₂O₅

Average Mass

296.2742 Da

Monoisotopic Mass

296.06847 Da

IUPAC Name

16-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13(18),14,16-heptaene

Traditional Name

anhydropisatin

CAS Registry Number

3187-53-9

SMILES

COC1=CC2=C(C=C1)C1=C(CO2)C2=CC3=C(OCO3)C=C2O1

InChI Identifier

InChI=1S/C17H12O5/c1-18-9-2-3-10-13(4-9)19-7-12-11-5-15-16(21-8-20-15)6-14(11)22-17(10)12/h2-6H,7-8H2,1H3

InChI Key

XWTCRKNSJARUIU-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, 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
Derris laxiflora	LOTUS Database	35616633
Derris urucu	Plant	KNApSAcK
Flemingia chappar	Plant	KNApSAcK
Millettia pachyloba	Plant	KNApSAcK
Pisum sativum	FooDB	KNAPSACK
Solori scandens	Plant	KNApSAcK
Styphnolobium japonicum	Plant	KNApSAcK
Tephrosia candida	LOTUS Database	35616633
Tephrosia purpurea	LOTUS Database	35616633
Tephrosia tinctoria	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
1-benzopyran
Benzopyran
Benzodioxole
Benzofuran
Anisole
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Furan
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070151 )

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	3.24	ALOGPS
logP	2.76	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	50.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.16 m³·mol⁻¹	ChemAxon
Polarizability	31.14 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

FDB001651

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

11822566

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Anhydropisatin (NP0045694)

MOL for NP0045694 (Anhydropisatin)

3D MOL for NP0045694 (Anhydropisatin)

3D SDF for NP0045694 (Anhydropisatin)

3D-SDF for NP0045694 (Anhydropisatin)

PDB for NP0045694 (Anhydropisatin)

3D PDB for NP0045694 (Anhydropisatin)

SMILES for NP0045694 (Anhydropisatin)

INCHI for NP0045694 (Anhydropisatin)

Structure for NP0045694 (Anhydropisatin)

3D Structure for NP0045694 (Anhydropisatin)