NP-MRD: Showing NP-Card for 4'-O-Demethyldehydropodophyllotoxin (NP0050463)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 21:44:13 UTC

Updated at

2022-04-27 21:44:13 UTC

NP-MRD ID

NP0050463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4'-O-Demethyldehydropodophyllotoxin

Description

10-Hydroxy-16-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,12-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8,10,15-pentaen-14-one belongs to the class of organic compounds known as furanonaphthodioxoles. These are aromatic heterocyclic compounds containing a 1,3-dioxole ring linearly fused to the a naphthofuran. 4'-O-Demethyldehydropodophyllotoxin is found in Podophyllum hexandrum . Based on a literature review very few articles have been published on 10-hydroxy-16-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,12-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8,10,15-pentaen-14-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223442D          

 29 33  0  0  0  0            999 V2000
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
  7 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  1 29  1  0  0  0  0
M  END


  Mrv1652304272223442D          

 29 33  0  0  0  0            999 V2000
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
  7 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  1 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)C1=C2C(=O)COC2=C(O)C2=CC3=C(OCO3)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C21H16O8/c1-25-15-3-9(4-16(26-2)20(15)24)17-10-5-13-14(29-8-28-13)6-11(10)19(23)21-18(17)12(22)7-27-21/h3-6,23-24H,7-8H2,1-2H3

> <INCHI_KEY>
OEQUUHXKRMMSOQ-UHFFFAOYSA-N

> <FORMULA>
C21H16O8

> <MOLECULAR_WEIGHT>
396.351

> <EXACT_MASS>
396.084517475

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
39.34852421199458

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-hydroxy-16-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,12-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8,10,15-pentaen-14-one

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
2.412013503333333

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.76539333374574

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.6747934374162705

> <JCHEM_PKA_STRONGEST_BASIC>
-4.278568136196891

> <JCHEM_POLAR_SURFACE_AREA>
103.68

> <JCHEM_REFRACTIVITY>
100.6064

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-hydroxy-16-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,12-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8,10,15-pentaen-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   8.233   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   9.003   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.591   9.003   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.591  10.543   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.924  10.543   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.257   9.003   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.257  10.543   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.390   4.089   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.295   2.843   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.390   1.597   0.000  0.00  0.00           O+0
CONECT    1    2    6   29                                                  
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   26                                                  
CONECT    8    7    9   25                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   14                                                            
CONECT   20   13   21                                                       
CONECT   21   20                                                            
CONECT   22    9   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24    8                                                       
CONECT   26    7                                                            
CONECT   27    2   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    1                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₁₆O₈

Average Mass

396.3510 Da

Monoisotopic Mass

396.08452 Da

IUPAC Name

10-hydroxy-16-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,12-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8,10,15-pentaen-14-one

Traditional Name

10-hydroxy-16-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,12-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8,10,15-pentaen-14-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)C1=C2C(=O)COC2=C(O)C2=CC3=C(OCO3)C=C12

InChI Identifier

InChI=1S/C21H16O8/c1-25-15-3-9(4-16(26-2)20(15)24)17-10-5-13-14(29-8-28-13)6-11(10)19(23)21-18(17)12(22)7-27-21/h3-6,23-24H,7-8H2,1-2H3

InChI Key

OEQUUHXKRMMSOQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Podophyllum hexandrum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanonaphthodioxoles. These are aromatic heterocyclic compounds containing a 1,3-dioxole ring linearly fused to the a naphthofuran.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Furanonaphthodioxoles

Direct Parent

Furanonaphthodioxoles

Alternative Parents

Substituents

Linear furanonaphthodioxole
Biphenol
1-naphthol
Methoxyphenol
Naphthalene
M-dimethoxybenzene
Dimethoxybenzene
Benzodioxole
Benzofuran
Coumaran
Anisole
Phenoxy compound
Methoxybenzene
Phenol ether
Aryl ketone
Aryl alkyl ketone
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ketone
Acetal
Oxacycle
Ether
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen 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	2.94	ALOGPS
logP	2.41	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.61 m³·mol⁻¹	ChemAxon
Polarizability	39.35 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

C00000694

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

163105345

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4'-O-Demethyldehydropodophyllotoxin (NP0050463)

MOL for NP0050463 (4'-O-Demethyldehydropodophyllotoxin)

3D MOL for NP0050463 (4'-O-Demethyldehydropodophyllotoxin)

3D SDF for NP0050463 (4'-O-Demethyldehydropodophyllotoxin)

3D-SDF for NP0050463 (4'-O-Demethyldehydropodophyllotoxin)

PDB for NP0050463 (4'-O-Demethyldehydropodophyllotoxin)

3D PDB for NP0050463 (4'-O-Demethyldehydropodophyllotoxin)

SMILES for NP0050463 (4'-O-Demethyldehydropodophyllotoxin)

INCHI for NP0050463 (4'-O-Demethyldehydropodophyllotoxin)

Structure for NP0050463 (4'-O-Demethyldehydropodophyllotoxin)

3D Structure for NP0050463 (4'-O-Demethyldehydropodophyllotoxin)