NP-MRD: Showing NP-Card for Haplodimerine (NP0051228)

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Record Information

Version

2.0

Created at

2022-04-27 22:37:19 UTC

Updated at

2022-04-27 22:37:19 UTC

NP-MRD ID

NP0051228

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Haplodimerine

Description

Haplodimerine 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. Haplodimerine is found in Haplophyllum foliosum and Haplophyllum griffithianum. Based on a literature review very few articles have been published on Haplodimerine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200372D          

 36 42  0  0  1  0            999 V2000
    7.6157   -0.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -0.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3443    0.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7210    1.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5450    1.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9923    0.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8163    0.4942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1929    1.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5203    0.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1437   -0.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5911   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4151   -1.0555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0701   -1.7360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3007   -1.4382    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3462   -0.6144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5225   -0.5689    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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   -0.7267   -2.0606   -2.3967 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282200372D          

 36 42  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0051228

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(OC)=C3[C@H]4[C@@H](OC3=NC2=C1OC)[C@@H]1[C@H]4C2=C(OC1(C)C)C1=CC=CC=C1NC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H26N2O6/c1-28(2)20-16(18-23(36-28)12-8-6-7-9-14(12)29-26(18)31)17-19-22(33-4)13-10-11-15(32-3)24(34-5)21(13)30-27(19)35-25(17)20/h6-11,16-17,20,25H,1-5H3,(H,29,31)/t16-,17+,20+,25-/m1/s1

> <INCHI_KEY>
ZTSCGHFGGQONGE-XHFAZCCNSA-N

> <FORMULA>
C28H26N2O6

> <MOLECULAR_WEIGHT>
486.524

> <EXACT_MASS>
486.179086565

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
49.611325648018614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,14R,15S)-4,8,9-trimethoxy-16,16-dimethyl-13,17-dioxa-11,25-diazaheptacyclo[13.12.0.0^{2,14}.0^{3,12}.0^{5,10}.0^{18,27}.0^{19,24}]heptacosa-3,5,7,9,11,18(27),19,21,23-nonaen-26-one

> <ALOGPS_LOGP>
4.20

> <JCHEM_LOGP>
3.0020460066666663

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.784751446303932

> <JCHEM_PKA_STRONGEST_BASIC>
2.789979649615452

> <JCHEM_POLAR_SURFACE_AREA>
88.14

> <JCHEM_REFRACTIVITY>
133.38779999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,14R,15S)-4,8,9-trimethoxy-16,16-dimethyl-13,17-dioxa-11,25-diazaheptacyclo[13.12.0.0^{2,14}.0^{3,12}.0^{5,10}.0^{18,27}.0^{19,24}]heptacosa-3,5,7,9,11,18(27),19,21,23-nonaen-26-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      14.216  -0.524   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.678  -0.600   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.843   0.694   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.546   2.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.084   2.140   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.919   0.846   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      16.457   0.922   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      17.160   2.293   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.305   0.618   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.602  -0.753   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.437  -2.047   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      11.975  -1.970   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       9.464  -3.241   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.028  -2.685   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.113  -1.147   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.575  -1.062   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.490  -2.600   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.116  -3.295   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.827  -2.452   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.912  -0.915   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.286  -0.220   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.371   1.318   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.745   2.013   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       4.082   2.160   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       2.708   1.465   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.623  -0.072   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.249  -0.768   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.040   0.075   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.045   1.612   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.419   2.308   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.763  -4.692   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.319  -4.613   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.470   1.911   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.931   1.835   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      15.051  -1.818   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      16.589  -1.742   0.000  0.00  0.00           C+0
CONECT    1    2    6   35                                                  
CONECT    2    1    3   12                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    3   10   33                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    2                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   10   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   14   18                                                  
CONECT   18   17   19   31   32                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   16   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   20   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   18                                                            
CONECT   32   18                                                            
CONECT   33    9   34                                                       
CONECT   34   33                                                            
CONECT   35    1   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₆N₂O₆

Average Mass

486.5240 Da

Monoisotopic Mass

486.17909 Da

IUPAC Name

(1S,2S,14R,15S)-4,8,9-trimethoxy-16,16-dimethyl-13,17-dioxa-11,25-diazaheptacyclo[13.12.0.0^{2,14}.0^{3,12}.0^{5,10}.0^{18,27}.0^{19,24}]heptacosa-3,5,7,9,11,18(27),19,21,23-nonaen-26-one

Traditional Name

(1S,2S,14R,15S)-4,8,9-trimethoxy-16,16-dimethyl-13,17-dioxa-11,25-diazaheptacyclo[13.12.0.0^{2,14}.0^{3,12}.0^{5,10}.0^{18,27}.0^{19,24}]heptacosa-3,5,7,9,11,18(27),19,21,23-nonaen-26-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(OC)=C3[C@H]4[C@@H](OC3=NC2=C1OC)[C@@H]1[C@H]4C2=C(OC1(C)C)C1=CC=CC=C1NC2=O

InChI Identifier

InChI=1S/C28H26N2O6/c1-28(2)20-16(18-23(36-28)12-8-6-7-9-14(12)29-26(18)31)17-19-22(33-4)13-10-11-15(32-3)24(34-5)21(13)30-27(19)35-25(17)20/h6-11,16-17,20,25H,1-5H3,(H,29,31)/t16-,17+,20+,25-/m1/s1

InChI Key

ZTSCGHFGGQONGE-XHFAZCCNSA-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
Haplophyllum foliosum	Plant	KNApSAcK
Haplophyllum griffithianum	LOTUS Database	35616633

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
Dihydrofuranoquinoline
Dihydroquinolone
Dihydroquinoline
Pyranopyridine
Anisole
Alkyl aryl ether
Pyridinone
Pyran
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous ester
Lactam
Oxacycle
Ether
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:5617 )
oxacycle (CHEBI:5617 )
organonitrogen heterocyclic compound (CHEBI:5617 )
Quinoline alkaloids (C10691 )

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	4.2	ALOGPS
logP	3	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	12.78	ChemAxon
pKa (Strongest Basic)	2.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	88.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	133.39 m³·mol⁻¹	ChemAxon
Polarizability	49.61 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00002170

Chemspider ID

391212

KEGG Compound ID

C10691

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442909

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Haplodimerine (NP0051228)

MOL for NP0051228 (Haplodimerine)

3D MOL for NP0051228 (Haplodimerine)

3D SDF for NP0051228 (Haplodimerine)

3D-SDF for NP0051228 (Haplodimerine)

PDB for NP0051228 (Haplodimerine)

3D PDB for NP0051228 (Haplodimerine)

SMILES for NP0051228 (Haplodimerine)

INCHI for NP0051228 (Haplodimerine)

Structure for NP0051228 (Haplodimerine)

3D Structure for NP0051228 (Haplodimerine)