NP-MRD: Showing NP-Card for Neohydroxylunine (NP0083578)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-29 04:34:39 UTC

Updated at

2022-04-29 04:34:39 UTC

NP-MRD ID

NP0083578

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neohydroxylunine

Description

Neohydroxylunine belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. Neohydroxylunine is found in Ptelea trifoliata . Neohydroxylunine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    1.1706   -1.9637    0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8180   -0.5679    0.3966 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4437   -0.1185    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7644    1.2001    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2286    2.0852   -0.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211    3.3080   -0.2193 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476    1.6526   -0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532    2.5277   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8409    2.0546   -0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1314    0.7087   -0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0933   -0.1278   -0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7795    0.3111    0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -1.4159    0.0613 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -1.4127   -0.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2969   -0.0542   -0.5062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1307    1.6845    0.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1785    0.6614    0.6707 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2998    0.9172   -0.1456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7672   -0.7500    0.4725 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8893   -1.0982   -0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6604   -1.7250    1.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448   -1.0229    0.8908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2373   -2.4852    0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8704   -2.0882    1.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5464   -2.4358   -0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3380    3.5727   -0.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6333    2.7452   -0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2214   -2.0574   -1.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5357   -1.7613    0.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802    2.2628   -0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1413    2.4323    1.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5792    0.7484    1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6391    1.8496    0.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9278   -0.8531   -1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0098   -2.1957   -1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7316   -0.6026   -1.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6138   -1.8958    0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799   -1.4012    2.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0943   -2.6890    1.2793 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 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  6
 19 21  1  0
 19 22  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 15  1  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 12  2  1  0
 22  3  1  0
 12  7  1  0
 11 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  1
 18 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
  8 26  1  0
  9 27  1  0
 14 28  1  0
 14 29  1  0
M  END


  Mrv1533004171506262D          

 22 25  0  0  0  0            999 V2000
    4.0045   -3.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7550   -2.4166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9492   -2.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -1.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -1.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3376   -1.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5872   -2.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7695   -2.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5528   -3.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3930   -2.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2559   -0.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0063   -0.0576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0616   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6179   -0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4236   -0.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6732   -1.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4245   -1.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3327   -2.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5246   -2.7016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1170   -1.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3112   -1.8073    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 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  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
  2 22  1  0  0  0  0
 14 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083578

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=C(CC(O)C(C)(C)O2)C(=O)C2=CC=C3OCOC3=C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO5/c1-16(2)11(18)6-9-13(19)8-4-5-10-14(21-7-20-10)12(8)17(3)15(9)22-16/h4-5,11,18H,6-7H2,1-3H3

> <INCHI_KEY>
KKFVJTACGUTIQR-UHFFFAOYSA-N

> <FORMULA>
C16H17NO5

> <MOLECULAR_WEIGHT>
303.314

> <EXACT_MASS>
303.110672651

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.194160951372613

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-6,6,9-trimethyl-7,12,14-trioxa-9-azatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1(17),3(8),10,15-tetraen-2-one

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
1.6467391319999996

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.89465909375867

> <JCHEM_PKA_STRONGEST_BASIC>
-3.282276112389958

> <JCHEM_POLAR_SURFACE_AREA>
68.23

> <JCHEM_REFRACTIVITY>
88.6951

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-6,6,9-trimethyl-7,12,14-trioxa-9-azatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1(17),3(8),10,15-tetraen-2-one

> <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  C   UNK     0       7.475  -5.979   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       7.009  -4.511   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.505  -4.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.039  -2.713   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.535  -2.382   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.497  -3.520   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.993  -3.189   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.963  -4.987   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.436  -5.191   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.898  -6.526   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.467  -5.318   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.078  -1.575   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.612  -0.107   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.582  -1.906   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.620  -0.768   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.124  -1.099   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.590  -2.567   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.992  -3.203   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.821  -4.733   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.313  -5.043   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.552  -3.704   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.048  -3.374   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8    3                                                       
CONECT   12    4   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17   22                                                  
CONECT   22   21    2   14                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₇NO₅

Average Mass

303.3140 Da

Monoisotopic Mass

303.11067 Da

IUPAC Name

5-hydroxy-6,6,9-trimethyl-7,12,14-trioxa-9-azatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1(17),3(8),10,15-tetraen-2-one

Traditional Name

5-hydroxy-6,6,9-trimethyl-7,12,14-trioxa-9-azatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁵]heptadeca-1(17),3(8),10,15-tetraen-2-one

CAS Registry Number

Not Available

SMILES

CN1C2=C(CC(O)C(C)(C)O2)C(=O)C2=CC=C3OCOC3=C12

InChI Identifier

InChI=1S/C16H17NO5/c1-16(2)11(18)6-9-13(19)8-4-5-10-14(21-7-20-10)12(8)17(3)15(9)22-16/h4-5,11,18H,6-7H2,1-3H3

InChI Key

KKFVJTACGUTIQR-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
Ptelea trifoliata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Pyranoquinolines

Alternative Parents

Substituents

Pyranoquinoline
Dihydroquinolone
Dihydroquinoline
Pyranopyridine
Benzodioxole
Alkyl aryl ether
Pyran
Pyridine
Benzenoid
Vinylogous amide
Heteroaromatic compound
Vinylogous ester
Secondary alcohol
Oxacycle
Azacycle
Acetal
Ether
Organic nitrogen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
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	1.7	ALOGPS
logP	1.65	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.7 m³·mol⁻¹	ChemAxon
Polarizability	31.19 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

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

14845310

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Neohydroxylunine (NP0083578)

MOL for NP0083578 (Neohydroxylunine)

3D MOL for NP0083578 (Neohydroxylunine)

3D SDF for NP0083578 (Neohydroxylunine)

3D-SDF for NP0083578 (Neohydroxylunine)

PDB for NP0083578 (Neohydroxylunine)

3D PDB for NP0083578 (Neohydroxylunine)

SMILES for NP0083578 (Neohydroxylunine)

INCHI for NP0083578 (Neohydroxylunine)

Structure for NP0083578 (Neohydroxylunine)

3D Structure for NP0083578 (Neohydroxylunine)