NP-MRD: Showing NP-Card for (1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol (NP0330329)

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Record Information

Version

1.0

Created at

2022-09-12 15:34:06 UTC

Updated at

2022-09-12 15:34:06 UTC

NP-MRD ID

NP0330329

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol

Description

(1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol is found in Fritillaria delavayi. Based on a literature review very few articles have been published on Delafrine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122217342D          

 31 36  0  0  1  0            999 V2000
    5.5937   -1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9765   -1.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5350   -0.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9178    0.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7421    0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1250    1.0453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6835    1.7423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9493    1.0792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3321    1.8100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8906    2.5069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1564    1.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5979    1.1469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4112    1.0087    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0582    1.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8250    1.2162    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4720    1.7281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9448    0.4000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   12.8315   -0.7206    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5983   -1.0249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1845   -1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4177   -0.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2979   -0.1119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6509   -0.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5311    0.1924    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7918   -0.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2151    0.4161    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3908    0.3823    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0079   -0.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1836   -0.3824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8008   -1.1132    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
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 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  1  0  0  0
 27 26  1  1  0  0  0
 12 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 31  1  0  0  0  0
M  END

     RDKit          3D

 76 81  0  0  0  0  0  0  0  0999 V2000
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    3.5006    0.2804   -0.2266 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309122217342D          

 31 36  0  0  1  0            999 V2000
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  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330329

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2[C@H](C)[C@H]3[C@@H](O)C[C@@H]4[C@@H](C[C@H]5[C@H]4C[C@@H](O)[C@H]4C[C@@H](O)CC[C@]54C)[C@@H]3CN2C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H45NO3/c1-14-4-5-23-15(2)26-20(13-28(23)12-14)17-9-21-19(18(17)10-25(26)31)11-24(30)22-8-16(29)6-7-27(21,22)3/h14-26,29-31H,4-13H2,1-3H3/t14?,15-,16-,17+,18+,19-,20-,21-,22+,23?,24+,25-,26+,27+/m0/s1

> <INCHI_KEY>
DRFSPDBMXZHMAP-BRYVYBRZSA-N

> <FORMULA>
C27H45NO3

> <MOLECULAR_WEIGHT>
431.661

> <EXACT_MASS>
431.339944313

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
52.917403037269466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,10R,11S,12S,14S,15S,17R,18S,20S,23R,24S)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosane-12,17,20-triol

> <JCHEM_LOGP>
2.6075969956666656

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.025157924629177

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.526121183713407

> <JCHEM_PKA_STRONGEST_BASIC>
10.539962692961467

> <JCHEM_POLAR_SURFACE_AREA>
63.93

> <JCHEM_REFRACTIVITY>
123.52509999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,10R,11S,12S,14S,15S,17R,18S,20S,23R,24S)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosane-12,17,20-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.442  -3.505   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.156  -2.141   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.332  -0.840   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.047   0.524   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.585   0.587   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.300   1.951   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.476   3.252   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.839   2.014   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.553   3.379   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.729   4.680   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      17.092   3.442   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.916   2.141   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.434   1.883   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.642   2.838   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.073   2.270   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      23.281   3.226   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      22.297   0.747   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.728   0.179   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.952  -1.345   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      25.384  -1.913   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      22.744  -2.301   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.313  -1.733   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.089  -0.209   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.882  -1.164   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.658   0.359   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.278  -0.324   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.201   0.777   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.663   0.714   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.948  -0.651   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      13.409  -0.714   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      12.695  -2.078   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   28                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   13   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   12   28                                                  
CONECT   28   27    8   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29    5   31                                                  
CONECT   31   30    2                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₅NO₃

Average Mass

431.6610 Da

Monoisotopic Mass

431.33994 Da

IUPAC Name

(1R,2S,10R,11S,12S,14S,15S,17R,18S,20S,23R,24S)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosane-12,17,20-triol

Traditional Name

(1R,2S,10R,11S,12S,14S,15S,17R,18S,20S,23R,24S)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosane-12,17,20-triol

CAS Registry Number

Not Available

SMILES

CC1CCC2[C@H](C)[C@H]3[C@@H](O)C[C@@H]4[C@@H](C[C@H]5[C@H]4C[C@@H](O)[C@H]4C[C@@H](O)CC[C@]54C)[C@@H]3CN2C1

InChI Identifier

InChI=1S/C27H45NO3/c1-14-4-5-23-15(2)26-20(13-28(23)12-14)17-9-21-19(18(17)10-25(26)31)11-24(30)22-8-16(29)6-7-27(21,22)3/h14-26,29-31H,4-13H2,1-3H3/t14?,15-,16-,17+,18+,19-,20-,21-,22+,23?,24+,25-,26+,27+/m0/s1

InChI Key

DRFSPDBMXZHMAP-BRYVYBRZSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Fritillaria delavayi	LOTUS Database	35616633

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	2.61	ChemAxon
pKa (Strongest Acidic)	14.53	ChemAxon
pKa (Strongest Basic)	10.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	63.93 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	123.53 m³·mol⁻¹	ChemAxon
Polarizability	52.92 Å³	ChemAxon
Number of Rings	6	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

C00028148

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

101189431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol (NP0330329)

MOL for NP0330329 ((1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol)

3D MOL for NP0330329 ((1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol)

3D SDF for NP0330329 ((1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol)

3D-SDF for NP0330329 ((1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol)

PDB for NP0330329 ((1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol)

3D PDB for NP0330329 ((1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol)

SMILES for NP0330329 ((1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol)

INCHI for NP0330329 ((1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol)

Structure for NP0330329 ((1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol)

3D Structure for NP0330329 ((1r,2s,10r,11s,12s,14s,15s,17r,18s,20s,23r,24s)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosane-12,17,20-triol)