NP-MRD: Showing NP-Card for [(1s,5r,12e,16r,17s)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid (NP0161148)

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Record Information

Version

2.0

Created at

2022-09-02 19:15:23 UTC

Updated at

2022-09-02 19:15:23 UTC

NP-MRD ID

NP0161148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,5r,12e,16r,17s)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid

Description

Based on a literature review very few articles have been published on 2-[(1S,5R,12Z,16R,17S)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]Henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022221152D          

 33 35  0  0  1  0            999 V2000
    3.4772    1.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933    0.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6732    0.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4967    0.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2384    0.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7373    0.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5558    0.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0548    1.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7854   -0.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0545   -1.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7486   -1.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5390   -2.4327    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.7154   -2.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4159   -1.7113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0258   -3.3011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4932   -3.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2459   -3.5702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4224   -3.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0336   -3.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5071   -2.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9401   -1.1258    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2757   -0.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4456   -1.7778    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  9 10  1  4  0  0  0
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 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
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  2 32  1  0  0  0  0
 31 33  1  1  0  0  0
 21 33  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309022221152D          

 33 35  0  0  1  0            999 V2000
    3.4772    1.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 31 33  1  1  0  0  0
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M  END
> <DATABASE_ID>
NP0161148

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=CC2=CSC(=N2)[C@@H](C)N=C(O)C[C@]2(CC(O)=O)CC[C@](C)(O)[C@@H](CC(=C)\C=C/1)S2

> <INCHI_IDENTIFIER>
InChI=1S/C25H34N2O4S2/c1-5-6-18-8-7-16(2)11-20-24(4,31)9-10-25(33-20,14-22(29)30)13-21(28)26-17(3)23-27-19(12-18)15-32-23/h7-8,12,15,17,20,31H,2,5-6,9-11,13-14H2,1,3-4H3,(H,26,28)(H,29,30)/b8-7-,18-12?/t17-,20-,24+,25+/m1/s1

> <INCHI_KEY>
AJDKITCLGCYCKZ-JWZKOMHBSA-N

> <FORMULA>
C25H34N2O4S2

> <MOLECULAR_WEIGHT>
490.68

> <EXACT_MASS>
490.195999931

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
52.414150612897885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1S,5R,12E,16R,17S)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1^{6,9}]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid

> <ALOGPS_LOGP>
3.95

> <JCHEM_LOGP>
1.6821258292669845

> <ALOGPS_LOGS>
-5.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.63106279330329

> <JCHEM_PKA_STRONGEST_ACIDIC>
-5.251145963897046

> <JCHEM_PKA_STRONGEST_BASIC>
15.10781364871183

> <JCHEM_POLAR_SURFACE_AREA>
103.01

> <JCHEM_REFRACTIVITY>
134.9477

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,5R,12E,16R,17S)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1^{6,9}]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.491   1.984   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.267   0.654   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.723   1.157   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.260   1.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.645   0.389   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.576   1.616   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.104   1.422   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.036   2.649   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.666  -0.763   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.168  -2.219   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.464  -3.052   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0      14.073  -4.541   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0      12.535  -4.629   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      11.976  -3.194   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      11.248  -6.162   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.121  -7.431   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       9.792  -6.664   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       8.255  -6.571   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.864  -8.061   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.871  -5.897   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.850  -4.744   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.314  -6.188   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.796  -6.447   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.261  -7.891   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.813  -5.261   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.324  -4.953   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.380  -3.736   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.962  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.457  -1.984   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.022  -0.771   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.488  -2.101   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.115  -0.367   0.000  0.00  0.00           C+0
HETATM   33  S   UNK     0       6.432  -3.319   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13   10                                                       
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   26   33                                             
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31    2                                                       
CONECT   33   31   21                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
2-[(1S,5R,12Z,16R,17S)-3,17-Dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1,]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetate	Generator

Chemical Formula

C₂₅H₃₄N₂O₄S₂

Average Mass

490.6800 Da

Monoisotopic Mass

490.19600 Da

IUPAC Name

2-[(1S,5R,12E,16R,17S)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1^{6,9}]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid

Traditional Name

[(1S,5R,12E,16R,17S)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1^{6,9}]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid

CAS Registry Number

Not Available

SMILES

CCCC1=CC2=CSC(=N2)[C@@H](C)N=C(O)C[C@]2(CC(O)=O)CC[C@](C)(O)[C@@H](CC(=C)\C=C/1)S2

InChI Identifier

InChI=1S/C25H34N2O4S2/c1-5-6-18-8-7-16(2)11-20-24(4,31)9-10-25(33-20,14-22(29)30)13-21(28)26-17(3)23-27-19(12-18)15-32-23/h7-8,12,15,17,20,31H,2,5-6,9-11,13-14H2,1,3-4H3,(H,26,28)(H,29,30)/b8-7-,18-12?/t17-,20-,24+,25+/m1/s1

InChI Key

AJDKITCLGCYCKZ-JWZKOMHBSA-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

Not Available

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	3.95	ALOGPS
logP	1.68	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	-5.3	ChemAxon
pKa (Strongest Basic)	15.11	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.01 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	134.95 m³·mol⁻¹	ChemAxon
Polarizability	52.41 Å³	ChemAxon
Number of Rings	3	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,5r,12e,16r,17s)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid (NP0161148)

MOL for NP0161148 ([(1s,5r,12e,16r,17s)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid)

3D MOL for NP0161148 ([(1s,5r,12e,16r,17s)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid)

3D SDF for NP0161148 ([(1s,5r,12e,16r,17s)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid)

3D-SDF for NP0161148 ([(1s,5r,12e,16r,17s)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid)

PDB for NP0161148 ([(1s,5r,12e,16r,17s)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid)

3D PDB for NP0161148 ([(1s,5r,12e,16r,17s)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid)

SMILES for NP0161148 ([(1s,5r,12e,16r,17s)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid)

INCHI for NP0161148 ([(1s,5r,12e,16r,17s)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid)

Structure for NP0161148 ([(1s,5r,12e,16r,17s)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid)

3D Structure for NP0161148 ([(1s,5r,12e,16r,17s)-3,17-dihydroxy-5,17-dimethyl-14-methylidene-11-propyl-7,20-dithia-4,21-diazatricyclo[14.3.1.1⁶,⁹]henicosa-3,6(21),8,10,12-pentaen-1-yl]acetic acid)