NP-MRD: Showing NP-Card for (+)-10-Hydroxyisotrilobine (NP0078133)

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Record Information

Version

2.0

Created at

2022-04-28 23:15:46 UTC

Updated at

2022-04-28 23:15:46 UTC

NP-MRD ID

NP0078133

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-10-Hydroxyisotrilobine

Description

(+)-10-Hydroxyisotrilobine is found in Cocculus orbiculatus. Based on a literature review very few articles have been published on (8S,21S)-13,27-dimethoxy-7,22-dimethyl-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.2¹⁶,¹⁹.1⁴,³⁰.1¹⁰,¹⁴.0³,⁸.0²⁵,³³.0²⁸,³²]Heptatriaconta-1(30),2,4(34),10(37),11,13,16,18,25,27,32,35-dodecaen-37-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201152D          

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M  END

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M  END


  Mrv1652304292201152D          

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    5.4121    2.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8338    3.3644    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6846    3.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2240    2.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0581    2.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5824    2.2624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3742    3.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2120    3.7891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8456    4.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0098    4.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4938    4.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6699    4.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3455    4.0493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5255    3.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2768    1.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9957    0.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5541    0.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2803   -0.5580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4695   -0.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4297    1.3138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8742    4.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3657    4.6506    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  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  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  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  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  1 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 24 35  1  6  0  0  0
 35 36  1  0  0  0  0
 22 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 20 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 21 42  1  0  0  0  0
  3 43  1  0  0  0  0
 43 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078133

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3[C@H](CC4=CC=C(OC5=C(O)C(C[C@@H]6N(C)CCC7=CC8=C(OC3=C1O8)C=C67)=CC=C5OC)C=C4)N(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C36H36N2O6/c1-37-13-11-21-17-29-30-19-25(21)26(37)16-23-7-10-28(40-3)34(33(23)39)42-24-8-5-20(6-9-24)15-27-32-22(12-14-38(27)2)18-31(41-4)35(43-29)36(32)44-30/h5-10,17-19,26-27,39H,11-16H2,1-4H3/t26-,27-/m0/s1

> <INCHI_KEY>
PWHKMZBEXOATRH-SVBPBHIXSA-N

> <FORMULA>
C36H36N2O6

> <MOLECULAR_WEIGHT>
592.692

> <EXACT_MASS>
592.257336887

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
65.12977082512185

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8S,21S)-13,27-dimethoxy-7,22-dimethyl-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.2^{16,19}.1^{4,30}.1^{10,14}.0^{3,8}.0^{25,33}.0^{28,32}]heptatriaconta-1(30),2,4(34),10,12,14(37),16,18,25(33),26,28(32),35-dodecaen-37-ol

> <ALOGPS_LOGP>
5.10

> <JCHEM_LOGP>
6.017081211333334

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.669925062635587

> <JCHEM_PKA_STRONGEST_BASIC>
6.696746032727507

> <JCHEM_POLAR_SURFACE_AREA>
72.86000000000001

> <JCHEM_REFRACTIVITY>
169.35189999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8S,21S)-13,27-dimethoxy-7,22-dimethyl-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.2^{16,19}.1^{4,30}.1^{10,14}.0^{3,8}.0^{25,33}.0^{28,32}]heptatriaconta-1(30),2,4(34),10,12,14(37),16,18,25(33),26,28(32),35-dodecaen-37-ol

> <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  C   UNK     0      17.594   4.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.170   5.834   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.723   6.040   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.687   4.828   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.136   3.363   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.584   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.120   1.515   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      19.202   0.390   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      20.709   0.704   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.169   2.180   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.748  -1.082   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.128   0.253   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.943  -0.815   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.064   0.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.528   0.413   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.759  -0.943   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.623  -2.251   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.189  -2.198   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.334  -0.250   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.038   0.663   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.490   2.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.506   3.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.103   4.879   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.890   6.280   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.478   6.479   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.485   5.259   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.042   5.449   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.020   4.223   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      15.632   6.894   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      17.196   7.073   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.645   8.122   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.085   7.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.122   9.170   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.584   8.991   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       9.978   7.559   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       8.448   7.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.983   3.036   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.459   1.572   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.501   0.411   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       7.990  -1.042   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       6.476  -1.325   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      12.002   2.452   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      20.298   7.468   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      19.349   8.681   0.000  0.00  0.00           C+0
CONECT    1    2    6   28                                                  
CONECT    2    1    3   30                                                  
CONECT    3    2    4   43                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16   20                                                       
CONECT   20   19   21   39                                                  
CONECT   21   20   22   42                                                  
CONECT   22   21   23   37                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   35                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27    1                                                       
CONECT   29   27   30   31                                                  
CONECT   30   29    2                                                       
CONECT   31   29   32                                                       
CONECT   32   31   25   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   24   36                                                  
CONECT   36   35                                                            
CONECT   37   22   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   20   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40                                                            
CONECT   42   21                                                            
CONECT   43    3   44                                                       
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₃₆N₂O₆

Average Mass

592.6920 Da

Monoisotopic Mass

592.25734 Da

IUPAC Name

(8S,21S)-13,27-dimethoxy-7,22-dimethyl-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.2^{16,19}.1^{4,30}.1^{10,14}.0^{3,8}.0^{25,33}.0^{28,32}]heptatriaconta-1(30),2,4(34),10,12,14(37),16,18,25(33),26,28(32),35-dodecaen-37-ol

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3[C@H](CC4=CC=C(OC5=C(O)C(C[C@@H]6N(C)CCC7=CC8=C(OC3=C1O8)C=C67)=CC=C5OC)C=C4)N(C)CC2

InChI Identifier

InChI=1S/C36H36N2O6/c1-37-13-11-21-17-29-30-19-25(21)26(37)16-23-7-10-28(40-3)34(33(23)39)42-24-8-5-20(6-9-24)15-27-32-22(12-14-38(27)2)18-31(41-4)35(43-29)36(32)44-30/h5-10,17-19,26-27,39H,11-16H2,1-4H3/t26-,27-/m0/s1

InChI Key

PWHKMZBEXOATRH-SVBPBHIXSA-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
Cocculus orbiculatus	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	5.1	ALOGPS
logP	6.02	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	8.67	ChemAxon
pKa (Strongest Basic)	6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.86 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	169.35 m³·mol⁻¹	ChemAxon
Polarizability	65.13 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

Not Available

Chemspider ID

9630960

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11456112

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-10-Hydroxyisotrilobine (NP0078133)

MOL for NP0078133 ((+)-10-Hydroxyisotrilobine)

3D MOL for NP0078133 ((+)-10-Hydroxyisotrilobine)

3D SDF for NP0078133 ((+)-10-Hydroxyisotrilobine)

3D-SDF for NP0078133 ((+)-10-Hydroxyisotrilobine)

PDB for NP0078133 ((+)-10-Hydroxyisotrilobine)

3D PDB for NP0078133 ((+)-10-Hydroxyisotrilobine)

SMILES for NP0078133 ((+)-10-Hydroxyisotrilobine)

INCHI for NP0078133 ((+)-10-Hydroxyisotrilobine)

Structure for NP0078133 ((+)-10-Hydroxyisotrilobine)

3D Structure for NP0078133 ((+)-10-Hydroxyisotrilobine)