NP-MRD: Showing NP-Card for Acerogenin E (NP0070825)

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Record Information

Version

2.0

Created at

2022-04-28 16:14:56 UTC

Updated at

2022-04-28 16:14:56 UTC

NP-MRD ID

NP0070825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acerogenin E

Description

3,17-Dihydroxytricyclo[12.3.1.1²,⁶]Nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one belongs to the class of organic compounds known as meta,meta-bridged biphenyls. These are cyclic diarylheptanoids where the two aryl groups are linked to each other by an ether group conjugated to their 3-position. Acerogenin E is found in Acer nikoense , Alnus japonica, Betula davurica, Betula ermanii, Betula maximowicziana and Betula pendula. 3,17-Dihydroxytricyclo[12.3.1.1²,⁶]Nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241508192D          

 22 24  0  0  0  0            999 V2000
    4.2821   -1.0770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9272   -0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1048   -0.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499    0.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2175    1.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8626    1.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3302    2.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1526    2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6202    3.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426    3.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8953    3.8211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8659    2.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6280    2.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5630    1.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0262    0.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6666   -0.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8438   -0.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736   -1.0690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2172    0.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7607    1.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948    0.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0399    1.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 19 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  2  0  0  0  0
  5 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070825

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2CCCCC(=O)CCC3=CC=C(O)C(=C3)C1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O3/c20-15-4-2-1-3-13-6-9-18(21)16(11-13)17-12-14(5-8-15)7-10-19(17)22/h6-7,9-12,21-22H,1-5,8H2

> <INCHI_KEY>
HJJZJFOFYZSPGU-UHFFFAOYSA-N

> <FORMULA>
C19H20O3

> <MOLECULAR_WEIGHT>
296.366

> <EXACT_MASS>
296.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.08518661429602

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,17-dihydroxytricyclo[12.3.1.1²,⁶]nonadeca-1(18),2(19),3,5,14,16-hexaen-9-one

> <ALOGPS_LOGP>
3.97

> <JCHEM_LOGP>
4.620083010333333

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.120917419231171

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.935645252517752

> <JCHEM_PKA_STRONGEST_BASIC>
-5.564186538245104

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
87.0826

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,17-dihydroxytricyclo[12.3.1.1²,⁶]nonadeca-1(18),2(19),3,5,14,16-hexaen-9-one

> <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  O   UNK     0       7.993  -2.010   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.331  -0.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.796  -0.499   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.133   0.891   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.006   2.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.344   3.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.216   4.819   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.752   4.698   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.624   5.967   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.159   5.845   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.005   7.133   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.950   4.357   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.372   3.767   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.251   2.232   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.116   0.957   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.444  -0.429   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.908  -0.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.404  -1.995   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.739   0.527   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.753   1.873   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.204   0.649   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.541   2.039   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19   14                                                       
CONECT   21   19    2   22                                                  
CONECT   22   21    5                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₃

Average Mass

296.3660 Da

Monoisotopic Mass

296.14124 Da

IUPAC Name

3,17-dihydroxytricyclo[12.3.1.1²,⁶]nonadeca-1(18),2(19),3,5,14,16-hexaen-9-one

Traditional Name

3,17-dihydroxytricyclo[12.3.1.1²,⁶]nonadeca-1(18),2(19),3,5,14,16-hexaen-9-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C2CCCCC(=O)CCC3=CC=C(O)C(=C3)C1=C2

InChI Identifier

InChI=1S/C19H20O3/c20-15-4-2-1-3-13-6-9-18(21)16(11-13)17-12-14(5-8-15)7-10-19(17)22/h6-7,9-12,21-22H,1-5,8H2

InChI Key

HJJZJFOFYZSPGU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acer nikoense	Plant	KNApSAcK
Alnus japonica	LOTUS Database	35616633
Betula davurica	LOTUS Database	35616633
Betula ermanii	LOTUS Database	35616633
Betula maximowicziana	LOTUS Database	35616633
Betula pendula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as meta,meta-bridged biphenyls. These are cyclic diarylheptanoids where the two aryl groups are linked to each other by an ether group conjugated to their 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Cyclic diarylheptanoids

Direct Parent

Meta,meta-bridged biphenyls

Alternative Parents

Substituents

Meta,meta-bridged biphenyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.97	ALOGPS
logP	4.62	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	8.94	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.08 m³·mol⁻¹	ChemAxon
Polarizability	32.09 Å³	ChemAxon
Number of Rings	3	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

10402312

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Acerogenin E (NP0070825)

MOL for NP0070825 (Acerogenin E)

3D MOL for NP0070825 (Acerogenin E)

3D SDF for NP0070825 (Acerogenin E)

3D-SDF for NP0070825 (Acerogenin E)

PDB for NP0070825 (Acerogenin E)

3D PDB for NP0070825 (Acerogenin E)

SMILES for NP0070825 (Acerogenin E)

INCHI for NP0070825 (Acerogenin E)

Structure for NP0070825 (Acerogenin E)

3D Structure for NP0070825 (Acerogenin E)