NP-MRD: Showing NP-Card for Haemoxiphidone (NP0084082)

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Record Information

Version

2.0

Created at

2022-04-29 04:55:40 UTC

Updated at

2022-04-29 04:55:40 UTC

NP-MRD ID

NP0084082

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Haemoxiphidone

Description

Haemoxiphidone belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group. Haemoxiphidone is found in Haemodorum simulans and Haemodorum spicatum. Haemoxiphidone was first documented in 2013 (PMID: 23972335). Based on a literature review very few articles have been published on Haemoxiphidone (PMID: 26090896).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    2.1962    4.5350    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1787    3.3198   -0.7163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282    2.4188   -0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1323    2.7729   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2185    1.7945   -0.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421    2.2082   -0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718    1.3238   -0.5470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8900    1.7899   -0.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2795   -0.0169   -0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3248   -0.9215   -0.3311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9318   -1.3209    0.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9675   -0.4212   -0.3566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6975   -1.7606   -0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3989   -2.1858   -0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7087   -1.3302   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0569   -1.8693   -0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -1.5616    0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1502   -2.0773    1.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6452   -2.9151    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8285   -3.2320   -1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5544   -2.7075   -1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4194    0.0098   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8985    0.4737   -0.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4753    0.9948   -0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6893    0.6610   -0.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3077    5.1457   -0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    5.1337   -0.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2300    4.3941    1.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3917    3.7983   -0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7117    3.2715   -0.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6843    1.1664   -0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2514   -2.3882    0.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2913   -1.1682    1.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8364   -0.6933    1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5370   -2.4649   -0.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1809   -3.2362   -0.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5606   -0.9187    1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7858   -1.8188    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6590   -3.3301    0.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2569   -3.8915   -1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9567   -2.9818   -1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  2  0
 22 24  1  0
 24 25  2  0
 22 23  1  0
 24  3  1  0
 23  5  2  0
 23 12  1  0
 21 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  8 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
M  END


  Mrv1652304292206552D          

 25 28  0  0  0  0            999 V2000
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  3  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
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 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
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 17 24  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
 14 25  1  0  0  0  0
  7 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084082

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=CC(O)=C(OC)C3=CC=C(C4=CC=CC=C4)C(C1=O)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C21H16O4/c1-24-17-11-13-10-16(22)21(25-2)15-9-8-14(12-6-4-3-5-7-12)19(18(13)15)20(17)23/h3-11,22H,1-2H3

> <INCHI_KEY>
PMDWWXHMCLGWNY-UHFFFAOYSA-N

> <FORMULA>
C21H16O4

> <MOLECULAR_WEIGHT>
332.355

> <EXACT_MASS>
332.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
35.41167542510068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-2,6-dimethoxy-9-phenyl-1H-phenalen-1-one

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
3.686714732333333

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.54830447452025

> <JCHEM_PKA_STRONGEST_BASIC>
-4.619863136074502

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
97.5681

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-2,6-dimethoxy-9-phenylphenalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   17    2   25                                                  
CONECT   25   24   14    7                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₁₆O₄

Average Mass

332.3550 Da

Monoisotopic Mass

332.10486 Da

IUPAC Name

5-hydroxy-2,6-dimethoxy-9-phenyl-1H-phenalen-1-one

Traditional Name

5-hydroxy-2,6-dimethoxy-9-phenylphenalen-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=CC(O)=C(OC)C3=CC=C(C4=CC=CC=C4)C(C1=O)=C23

InChI Identifier

InChI=1S/C21H16O4/c1-24-17-11-13-10-16(22)21(25-2)15-9-8-14(12-6-4-3-5-7-12)19(18(13)15)20(17)23/h3-11,22H,1-2H3

InChI Key

PMDWWXHMCLGWNY-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
Haemodorum simulans	Plant	KNApSAcK
Haemodorum spicatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenylnaphthalene
Phenalen-1-one
Phenalen
2-naphthol
Anisole
Phenol ether
Aryl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Ketone
Ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	4.08	ALOGPS
logP	3.69	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	9.55	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.57 m³·mol⁻¹	ChemAxon
Polarizability	35.41 Å³	ChemAxon
Number of Rings	4	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

C00053291

Chemspider ID

58978972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73212250

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Brkljaca R, Urban S: HPLC-NMR and HPLC-MS Profiling and Bioassay-Guided Identification of Secondary Metabolites from the Australian Plant Haemodorum spicatum. J Nat Prod. 2015 Jul 24;78(7):1486-94. doi: 10.1021/np500905g. Epub 2015 Jun 19. [PubMed:26090896 ]
Urban S, Brkljaca R, White JM, Timmers MA: Phenylphenalenones and oxabenzochrysenones from the Australian plant Haemodorum simulans. Phytochemistry. 2013 Nov;95:351-9. doi: 10.1016/j.phytochem.2013.07.019. Epub 2013 Aug 20. [PubMed:23972335 ]

Showing NP-Card for Haemoxiphidone (NP0084082)

MOL for NP0084082 (Haemoxiphidone)

3D MOL for NP0084082 (Haemoxiphidone)

3D SDF for NP0084082 (Haemoxiphidone)

3D-SDF for NP0084082 (Haemoxiphidone)

PDB for NP0084082 (Haemoxiphidone)

3D PDB for NP0084082 (Haemoxiphidone)

SMILES for NP0084082 (Haemoxiphidone)

INCHI for NP0084082 (Haemoxiphidone)

Structure for NP0084082 (Haemoxiphidone)

3D Structure for NP0084082 (Haemoxiphidone)