NP-MRD: Showing NP-Card for Alnusdiol (NP0140030)

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Record Information

Version

2.0

Created at

2022-06-29 20:42:53 UTC

Updated at

2022-06-29 20:42:53 UTC

NP-MRD ID

NP0140030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Alnusdiol

Description

Alnusdiol 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. Alnusdiol is found in Alnus japonica, Betula maximowicziana and Casuarina junghuhniana. Alnusdiol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          2D

 45 47  0  0  0  0  0  0  0  0999 V2000
   -1.5000    2.5981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2423   -0.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4042   -1.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9921   -2.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0022   -1.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8214    0.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4414    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2606    2.2475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8714   -3.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0697   -5.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7707   -5.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2957   -7.4070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2719   -6.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833   -5.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5240   -5.8189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9844   -4.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2250   -2.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    3.8971    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0934   -0.2424    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3822   -1.9065    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0206    1.0716    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4598    3.1486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7143   -4.8415    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3122   -3.5491    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4094   -6.4008    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2217   -5.6206    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6111   -6.8616    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904   -8.5298    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5048   -6.9868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4271   -7.0165    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3279   -6.5917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830   -7.2753    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4797   -4.0838    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8629   -5.0417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869   -1.7732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6058   -3.3079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 22  1  0
 22 23  1  0
 23  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2  7  1  0
  7  6  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 19 20  1  0
  6  5  1  0
 13  8  1  0
 21 41  1  0
 20 40  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 23 45  1  0
  4 26  1  0
  3 25  1  0
  1 24  1  0
  6 27  1  0
  9 28  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
M  END


  Mrv1533004171507032D          

 23 25  0  0  0  0            999 V2000
    5.8953    3.8211    0.0000 O   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
    5.8659    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
    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
    4.5075    1.7719    0.0000 O   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
    2.7499    0.4776    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
    3.9272   -0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2821   -1.0770    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
 10 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
 17 19  1  0  0  0  0
  2 19  1  0  0  0  0
 14 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CCC2=CC=C(O)C(=C2)C2=CC(CCC(O)C1)=CC=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O4/c20-14-5-1-12-3-7-18(22)16(9-12)17-10-13(4-8-19(17)23)2-6-15(21)11-14/h3-4,7-10,14-15,20-23H,1-2,5-6,11H2

> <INCHI_KEY>
YWQBDYGHWGZJOM-UHFFFAOYSA-N

> <FORMULA>
C19H22O4

> <MOLECULAR_WEIGHT>
314.381

> <EXACT_MASS>
314.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.6908385521638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2(19),3,5,14,16-hexaene-3,9,11,17-tetrol

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
2.953069675666667

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.351354871898875

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.492036502568844

> <JCHEM_PKA_STRONGEST_BASIC>
-2.725857476897267

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
89.73660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2(19),3,5,14,16-hexaene-3,9,11,17-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0      11.005   7.133   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.159   5.845   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.950   4.357   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.372   3.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.251   2.232   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.116   0.957   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.444  -0.429   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.908  -0.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.404  -1.995   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.739   0.527   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.753   1.873   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.204   0.649   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.541   2.039   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.006   2.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.344   3.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.216   4.819   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.752   4.698   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.414   3.308   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.624   5.967   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.133   0.891   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.796  -0.499   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.331  -0.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.993  -2.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13   22                                                  
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    2                                                       
CONECT   20   14   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   12   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₄

Average Mass

314.3810 Da

Monoisotopic Mass

314.15181 Da

IUPAC Name

tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2(19),3,5,14,16-hexaene-3,9,11,17-tetrol

Traditional Name

tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2(19),3,5,14,16-hexaene-3,9,11,17-tetrol

CAS Registry Number

Not Available

SMILES

OC1CCC2=CC=C(O)C(=C2)C2=CC(CCC(O)C1)=CC=C2O

InChI Identifier

InChI=1S/C19H22O4/c20-14-5-1-12-3-7-18(22)16(9-12)17-10-13(4-8-19(17)23)2-6-15(21)11-14/h3-4,7-10,14-15,20-23H,1-2,5-6,11H2

InChI Key

YWQBDYGHWGZJOM-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, 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
Alnus japonica	LOTUS Database	35616633
Betula maximowicziana	LOTUS Database	35616633
Casuarina junghuhniana	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
Secondary alcohol
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	2.22	ALOGPS
logP	2.95	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.74 m³·mol⁻¹	ChemAxon
Polarizability	33.69 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

14704508

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Alnusdiol (NP0140030)

MOL for NP0140030 (Alnusdiol)

3D MOL for NP0140030 (Alnusdiol)

3D SDF for NP0140030 (Alnusdiol)

3D-SDF for NP0140030 (Alnusdiol)

PDB for NP0140030 (Alnusdiol)

3D PDB for NP0140030 (Alnusdiol)

SMILES for NP0140030 (Alnusdiol)

INCHI for NP0140030 (Alnusdiol)

Structure for NP0140030 (Alnusdiol)

3D Structure for NP0140030 (Alnusdiol)