NP-MRD: Showing NP-Card for 11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol (NP0222298)

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Record Information

Version

2.0

Created at

2022-09-06 00:06:02 UTC

Updated at

2022-09-06 00:06:02 UTC

NP-MRD ID

NP0222298

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol

Description

11-Benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]Docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone. 11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol is found in Didemnum molle. 11-Benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]Docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161514492D          

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M  END

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M  END


  Mrv1533004161514492D          

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 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 19 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 29 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
  4 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0222298

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C1NC(=O)C(CC2=CC=CC=C2)NC(=O)C2=CSC(=N2)C(C)NC(=O)C2=CSC(=N2)C(C)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28N6O5S2/c1-12-24-30-18(11-38-24)22(35)28-16(9-15-7-5-4-6-8-15)20(33)31-19(14(3)32)23(36)27-13(2)25-29-17(10-37-25)21(34)26-12/h4-8,10-14,16,19,32H,9H2,1-3H3,(H,26,34)(H,27,36)(H,28,35)(H,31,33)

> <INCHI_KEY>
ARCFFCLBNNIVPM-UHFFFAOYSA-N

> <FORMULA>
C25H28N6O5S2

> <MOLECULAR_WEIGHT>
556.66

> <EXACT_MASS>
556.156260374

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
55.97619726436875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),5(22),7,18(21)-tetraene-2,9,12,15-tetrone

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
0.9236799863333336

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.250369741784132

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.739675410619247

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8276772261997315

> <JCHEM_POLAR_SURFACE_AREA>
162.41

> <JCHEM_REFRACTIVITY>
139.6663

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),5(22),7,18(21)-tetraene-2,9,12,15-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       8.818  -5.442   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.146  -4.661   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.486  -5.420   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      10.133  -3.121   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      11.460  -2.340   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      12.800  -3.099   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.813  -4.639   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.128  -2.319   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.468  -3.078   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.480  -4.617   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.820  -5.377   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.833  -6.916   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.505  -7.697   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.166  -6.938   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.153  -5.398   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      14.115  -0.779   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      15.442   0.002   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.782  -0.757   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      15.430   1.542   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.451   2.695   0.000  0.00  0.00           C+0
HETATM   21  S   UNK     0      15.670   4.022   0.000  0.00  0.00           S+0
HETATM   22  C   UNK     0      14.077   3.841   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      14.090   2.301   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      12.737   4.600   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.725   6.140   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      11.410   3.819   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      10.070   4.578   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.057   6.118   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.743   3.798   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.234   4.105   0.000  0.00  0.00           C+0
HETATM   31  S   UNK     0       6.475   2.765   0.000  0.00  0.00           S+0
HETATM   32  C   UNK     0       7.428   1.477   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       8.755   2.258   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       7.441  -0.063   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.113  -0.844   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       8.780  -0.822   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       8.793  -2.362   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.466  -3.143   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   37                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    8   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   19                                                       
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32   29                                                       
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36    4   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈N₆O₅S₂

Average Mass

556.6600 Da

Monoisotopic Mass

556.15626 Da

IUPAC Name

11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),5(22),7,18(21)-tetraene-2,9,12,15-tetrone

Traditional Name

11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),5(22),7,18(21)-tetraene-2,9,12,15-tetrone

CAS Registry Number

Not Available

SMILES

CC(O)C1NC(=O)C(CC2=CC=CC=C2)NC(=O)C2=CSC(=N2)C(C)NC(=O)C2=CSC(=N2)C(C)NC1=O

InChI Identifier

InChI=1S/C25H28N6O5S2/c1-12-24-30-18(11-38-24)22(35)28-16(9-15-7-5-4-6-8-15)20(33)31-19(14(3)32)23(36)27-13(2)25-29-17(10-37-25)21(34)26-12/h4-8,10-14,16,19,32H,9H2,1-3H3,(H,26,34)(H,27,36)(H,28,35)(H,31,33)

InChI Key

ARCFFCLBNNIVPM-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, 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
Didemnum molle	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cyclic peptides

Alternative Parents

Substituents

Cyclic alpha peptide
Monocyclic benzene moiety
Benzenoid
Azole
Heteroaromatic compound
Thiazole
Cyclic carboximidic acid
Secondary alcohol
Polyol
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
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	1.48	ALOGPS
logP	0.92	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.74	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.41 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	139.67 m³·mol⁻¹	ChemAxon
Polarizability	55.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

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

72759147

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol (NP0222298)

MOL for NP0222298 (11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

3D MOL for NP0222298 (11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

3D SDF for NP0222298 (11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

3D-SDF for NP0222298 (11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

PDB for NP0222298 (11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

3D PDB for NP0222298 (11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

SMILES for NP0222298 (11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

INCHI for NP0222298 (11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

Structure for NP0222298 (11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)

3D Structure for NP0222298 (11-benzyl-14-(1-hydroxyethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol)