NP-MRD: Showing NP-Card for 16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate (NP0224911)

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Record Information

Version

2.0

Created at

2022-09-06 03:28:41 UTC

Updated at

2022-09-06 03:28:41 UTC

NP-MRD ID

NP0224911

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate

Description

16-Methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]Icosa-1(12),2,4(8),9,13,15,17-heptaen-15-yl acetate belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. 16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate is found in Swartzia leiocalycina. 16-Methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]Icosa-1(12),2,4(8),9,13,15,17-heptaen-15-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241502442D          

 27 31  0  0  0  0            999 V2000
    0.6685   -3.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0303   -2.7553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8533   -2.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3145   -3.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -3.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5987   -4.0087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4217   -3.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8829   -4.6354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7835   -3.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3223   -2.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8304   -1.8759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6056   -2.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3341   -1.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0336   -2.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8267   -1.9812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2879   -2.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7798   -3.3152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0047   -3.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2761   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5766   -2.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4993   -2.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0381   -1.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2151   -1.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -1.2725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9310   -1.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4698   -0.6458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691   -2.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  9 20  1  0  0  0  0
 12 20  1  0  0  0  0
 10 21  1  0  0  0  0
  5 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END


  Mrv1533004241502442D          

 27 31  0  0  0  0            999 V2000
    0.6685   -3.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0303   -2.7553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8533   -2.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3145   -3.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -3.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5987   -4.0087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4217   -3.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8829   -4.6354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7835   -3.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3223   -2.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8304   -1.8759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6056   -2.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3341   -1.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0336   -2.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8267   -1.9812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2879   -2.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7798   -3.3152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0047   -3.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2761   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5766   -2.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4993   -2.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0381   -1.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2151   -1.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -1.2725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9310   -1.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4698   -0.6458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691   -2.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  9 20  1  0  0  0  0
 12 20  1  0  0  0  0
 10 21  1  0  0  0  0
  5 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224911

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC(C)=O)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O8/c1-8(20)25-16-4-10-12(5-13(16)22-2)27-19(21)17-9-3-14-15(24-7-23-14)6-11(9)26-18(10)17/h3-6H,7H2,1-2H3

> <INCHI_KEY>
MJTAJNKJTVEHMY-UHFFFAOYSA-N

> <FORMULA>
C19H12O8

> <MOLECULAR_WEIGHT>
368.297

> <EXACT_MASS>
368.053217346

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
36.62310358800859

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-methoxy-20-oxo-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-heptaen-15-yl acetate

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.0772751419999995

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0464782616176413

> <JCHEM_POLAR_SURFACE_AREA>
93.43

> <JCHEM_REFRACTIVITY>
89.02019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-methoxy-20-oxo-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-heptaen-15-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.248  -6.527   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.923  -5.143   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.460  -5.036   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.320  -6.313   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.857  -6.206   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.718  -7.483   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.254  -7.376   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.115  -8.653   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.929  -5.992   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.068  -4.715   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.017  -3.502   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.464  -4.029   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.824  -3.306   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.129  -4.122   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.610  -3.698   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      15.471  -4.975   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.522  -6.188   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.075  -5.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.715  -6.384   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.410  -5.568   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.532  -4.822   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.671  -3.545   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.135  -3.652   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.274  -2.375   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.738  -2.482   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.877  -1.205   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.062  -3.866   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    9   12                                                  
CONECT   21   10    5   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
16-Methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0,.0,.0,]icosa-1(12),2,4(8),9,13,15,17-heptaen-15-yl acetic acid	Generator
16-Methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2,4(8),9,13,15,17-heptaen-15-yl acetic acid	Generator

Chemical Formula

C₁₉H₁₂O₈

Average Mass

368.2970 Da

Monoisotopic Mass

368.05322 Da

IUPAC Name

16-methoxy-20-oxo-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-heptaen-15-yl acetate

Traditional Name

16-methoxy-20-oxo-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-heptaen-15-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC(C)=O)C1=C(C3=CC4=C(OCO4)C=C3O1)C(=O)O2

InChI Identifier

InChI=1S/C19H12O8/c1-8(20)25-16-4-10-12(5-13(16)22-2)27-19(21)17-9-3-14-15(24-7-23-14)6-11(9)26-18(10)17/h3-6H,7H2,1-2H3

InChI Key

MJTAJNKJTVEHMY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Swartzia leiocalycina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Benzodioxole
Furopyran
Benzofuran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Furan
Heteroaromatic compound
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Acetal
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	2.73	ALOGPS
logP	2.08	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	93.43 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.02 m³·mol⁻¹	ChemAxon
Polarizability	36.62 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate (NP0224911)

MOL for NP0224911 (16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate)

3D MOL for NP0224911 (16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate)

3D SDF for NP0224911 (16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate)

3D-SDF for NP0224911 (16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate)

PDB for NP0224911 (16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate)

3D PDB for NP0224911 (16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate)

SMILES for NP0224911 (16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate)

INCHI for NP0224911 (16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate)

Structure for NP0224911 (16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate)

3D Structure for NP0224911 (16-methoxy-20-oxo-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-15-yl acetate)