NP-MRD: Showing NP-Card for 19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one (NP0165950)

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Record Information

Version

2.0

Created at

2022-09-03 01:13:20 UTC

Updated at

2022-09-03 01:13:21 UTC

NP-MRD ID

NP0165950

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one

Description

19-Ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]Nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. 19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one is found in Sarcocephalus latifolius. 19-Ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]Nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241502072D          

 36 42  0  0  0  0            999 V2000
   15.8195    0.9702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv1533004241502072D          

 36 42  0  0  0  0            999 V2000
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 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 23 31  1  0  0  0  0
 26 31  1  0  0  0  0
 20 32  1  0  0  0  0
 16 32  1  0  0  0  0
 32 33  2  0  0  0  0
 17 34  1  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0165950

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC2OC3OC(OC2C(O)C1O)C1=C(C=C2N(CCC4=C2NC2=CC=CC=C42)C1=O)C3C=C

> <INCHI_IDENTIFIER>
InChI=1S/C26H26N2O8/c1-2-11-14-9-16-19-13(12-5-3-4-6-15(12)27-19)7-8-28(16)23(32)18(14)25-34-22-21(31)20(30)17(10-29)33-26(22)36-24(11)35-25/h2-6,9,11,17,20-22,24-27,29-31H,1,7-8,10H2

> <INCHI_KEY>
QBVLOMJKKLVAPJ-UHFFFAOYSA-N

> <FORMULA>
C26H26N2O8

> <MOLECULAR_WEIGHT>
494.5

> <EXACT_MASS>
494.168915805

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
51.22711834182758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
0.17845116966666733

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.125055141977402

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.518920646855705

> <JCHEM_PKA_STRONGEST_BASIC>
-2.49987656127519

> <JCHEM_POLAR_SURFACE_AREA>
133.71

> <JCHEM_REFRACTIVITY>
126.467

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0      29.530   1.811   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      28.219   2.619   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.863   1.888   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      25.553   2.696   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      24.197   1.965   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      23.242   3.172   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      21.733   3.483   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      22.224   1.251   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      21.606  -0.949   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      23.129  -0.725   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      24.153   0.425   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.464  -0.383   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      25.419  -1.922   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      26.819   0.348   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      28.130  -0.460   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      20.295  -0.141   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.810   1.321   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.302   1.632   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.278   0.481   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      17.763  -0.981   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      16.740  -2.131   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.231  -1.820   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.747  -0.359   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.770   0.792   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      14.992   2.121   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      13.487   1.791   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.236   2.689   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.833   2.054   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.681   0.522   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.933  -0.376   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.336   0.259   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.271  -1.292   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      19.756  -2.753   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      20.378   2.752   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      19.227   3.775   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      19.538   5.284   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   34                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    3   15                                                  
CONECT   15   14                                                            
CONECT   16    9   17   32                                                  
CONECT   17   16   18   34                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   32                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   19   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   23   26                                                  
CONECT   32   20   16   33                                                  
CONECT   33   32                                                            
CONECT   34   17    7   35                                                  
CONECT   35   34   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

C₂₆H₂₆N₂O₈

Average Mass

494.5000 Da

Monoisotopic Mass

494.16892 Da

IUPAC Name

19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one

Traditional Name

19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one

CAS Registry Number

Not Available

SMILES

OCC1OC2OC3OC(OC2C(O)C1O)C1=C(C=C2N(CCC4=C2NC2=CC=CC=C42)C1=O)C3C=C

InChI Identifier

InChI=1S/C26H26N2O8/c1-2-11-14-9-16-19-13(12-5-3-4-6-15(12)27-19)7-8-28(16)23(32)18(14)25-34-22-21(31)20(30)17(10-29)33-26(22)36-24(11)35-25/h2-6,9,11,17,20-22,24-27,29-31H,1,7-8,10H2

InChI Key

QBVLOMJKKLVAPJ-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
Sarcocephalus latifolius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Pyranopyridine
3-alkylindole
Indole
Pyridinone
Monosaccharide
Oxane
Pyridine
Benzenoid
Heteroaromatic compound
Pyrrole
Secondary alcohol
Lactam
Oxacycle
Azacycle
Acetal
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organonitrogen compound
Primary alcohol
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
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	0.89	ALOGPS
logP	0.18	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.52	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.71 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	126.47 m³·mol⁻¹	ChemAxon
Polarizability	51.23 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

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 19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one (NP0165950)

MOL for NP0165950 (19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one)

3D MOL for NP0165950 (19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one)

3D SDF for NP0165950 (19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one)

3D-SDF for NP0165950 (19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one)

PDB for NP0165950 (19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one)

3D PDB for NP0165950 (19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one)

SMILES for NP0165950 (19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one)

INCHI for NP0165950 (19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one)

Structure for NP0165950 (19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one)

3D Structure for NP0165950 (19-ethenyl-25,26-dihydroxy-24-(hydroxymethyl)-21,23,28,29-tetraoxa-4,14-diazaheptacyclo[18.8.1.0²,¹⁸.0⁴,¹⁶.0⁷,¹⁵.0⁸,¹³.0²²,²⁷]nonacosa-2(18),7(15),8,10,12,16-hexaen-3-one)