NP-MRD: Showing NP-Card for (-)-Hongconin (NP0070651)

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Record Information

Version

2.0

Created at

2022-04-28 16:06:03 UTC

Updated at

2022-04-28 16:06:03 UTC

NP-MRD ID

NP0070651

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Hongconin

Description

(?)-Hongconin belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. (-)-Hongconin is found in Eleutherine americana MERR.et HEYNE and Eleutherine bulbosa. (-)-Hongconin was first documented in 2008 (PMID: 18758108). Based on a literature review a small amount of articles have been published on (?)-Hongconin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -4.7127    1.5519    0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3631    1.1986   -0.2262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7595    0.2989    0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4566   -0.2418    1.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9234   -1.1350    2.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6124   -1.5034    2.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8716   -0.9997    1.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4528   -1.4168    1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0053   -2.3049    2.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2002   -0.9113    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6588   -0.0184   -0.6915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6742    0.4007   -0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1179    1.2756   -1.4721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4197   -0.1076    0.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4637    0.5148   -1.7834 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5376    2.0291   -1.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7178    0.0315   -1.9510 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3918   -0.2711   -0.7730 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7713   -0.7320   -1.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875   -1.3037   -0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0108   -2.3920    0.3541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0271    2.3940   -0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3672    0.6556   -0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8611    1.9279    1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4937    0.0750    1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5199   -1.5409    3.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1391   -2.2065    3.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8963   -2.6752    2.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136    1.7563   -1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8920    0.2627   -2.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4205    2.3044   -2.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6250    2.4424   -0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6704    2.4707   -2.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4395    0.6636   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1114   -1.4322   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000   -1.2011   -2.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4798    0.1399   -1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 14  2  0
 14 12  1  0
 12 13  1  0
 12 11  2  0
 11 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 10  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  7 14  1  0
 10 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 13 29  1  0
 15 30  1  6
 16 31  1  0
 16 32  1  0
 16 33  1  0
 18 34  1  1
 19 35  1  0
 19 36  1  0
 19 37  1  0
  9 28  1  0
  6 27  1  0
  5 26  1  0
  4 25  1  0
M  END


  Mrv1652304282218062D          

 21 23  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    3.5724    2.0625    0.0000 O   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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    2.1434    2.0625    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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 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
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 16 20  1  1  0  0  0
  9 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070651

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(O)=C3[C@@H](C)O[C@H](C)C(=O)C3=C(O)C2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O5/c1-7-11-13(14(17)8(2)21-7)15(18)9-5-4-6-10(20-3)12(9)16(11)19/h4-8,18-19H,1-3H3/t7-,8-/m1/s1

> <INCHI_KEY>
VORNLKKDOSQORZ-HTQZYQBOSA-N

> <FORMULA>
C16H16O5

> <MOLECULAR_WEIGHT>
288.299

> <EXACT_MASS>
288.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.408135492602824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R)-5,10-dihydroxy-9-methoxy-1,3-dimethyl-1H,3H,4H-naphtho[2,3-c]pyran-4-one

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.9680132083333333

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.895867561988775

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.040353566689364

> <JCHEM_PKA_STRONGEST_BASIC>
-4.155034203831145

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
77.25670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R)-5,10-dihydroxy-9-methoxy-1,3-dimethyl-1H,3H-naphtho[2,3-c]pyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10   21                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   10   19                                                  
CONECT   19   18                                                            
CONECT   20   16                                                            
CONECT   21    9                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₅

Average Mass

288.2990 Da

Monoisotopic Mass

288.09977 Da

IUPAC Name

(1R,3R)-5,10-dihydroxy-9-methoxy-1,3-dimethyl-1H,3H,4H-naphtho[2,3-c]pyran-4-one

Traditional Name

(1R,3R)-5,10-dihydroxy-9-methoxy-1,3-dimethyl-1H,3H-naphtho[2,3-c]pyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=C2C(O)=C3[C@@H](C)O[C@H](C)C(=O)C3=C(O)C2=CC=C1

InChI Identifier

InChI=1S/C16H16O5/c1-7-11-13(14(17)8(2)21-7)15(18)9-5-4-6-10(20-3)12(9)16(11)19/h4-8,18-19H,1-3H3/t7-,8-/m1/s1

InChI Key

VORNLKKDOSQORZ-HTQZYQBOSA-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
Eleutherine americana MERR.et HEYNE	Plant	KNApSAcK
Eleutherine bulbosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
1-naphthol
Naphthalene
Benzopyran
Isochromane
2-benzopyran
Anisole
Hydroquinone
Phenol ether
Aryl alkyl ketone
Aryl ketone
Phenol
Alkyl aryl ether
Pyran
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Dialkyl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	2.78	ALOGPS
logP	2.97	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.04	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.26 m³·mol⁻¹	ChemAxon
Polarizability	29.41 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

C00029281

Chemspider ID

8283673

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bracket

METLIN ID

Not Available

PubChem Compound

10108147

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Han AR, Min HY, Nam JW, Lee NY, Wiryawan A, Suprapto W, Lee SK, Lee KR, Seo EK: Identification of a new naphthalene and its derivatives from the bulb of eleutherine americana with inhibitory activity on lipopolysaccharide-induced nitric oxide production. Chem Pharm Bull (Tokyo). 2008 Sep;56(9):1314-6. doi: 10.1248/cpb.56.1314. [PubMed:18758108 ]

Showing NP-Card for (-)-Hongconin (NP0070651)

MOL for NP0070651 ((-)-Hongconin)

3D MOL for NP0070651 ((-)-Hongconin)

3D SDF for NP0070651 ((-)-Hongconin)

3D-SDF for NP0070651 ((-)-Hongconin)

PDB for NP0070651 ((-)-Hongconin)

3D PDB for NP0070651 ((-)-Hongconin)

SMILES for NP0070651 ((-)-Hongconin)

INCHI for NP0070651 ((-)-Hongconin)

Structure for NP0070651 ((-)-Hongconin)

3D Structure for NP0070651 ((-)-Hongconin)