NP-MRD: Showing NP-Card for 19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one (NP0304480)

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Record Information

Version

2.0

Created at

2022-09-10 19:36:14 UTC

Updated at

2022-09-10 19:36:14 UTC

NP-MRD ID

NP0304480

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one

Description

19-Ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4(9),5,7,15-pentaen-14-one belongs to the class of organic compounds known as sulfuric acid monoesters. These are organic compounds containing the sulfuric acid monoester functional group, with the generic structure ROS(O)(=O)=O, (R=organyl group). 19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one is found in Sarcocephalus latifolius. 19-Ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4(9),5,7,15-pentaen-14-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161521312D          

 37 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161521312D          

 37 42  0  0  0  0            999 V2000
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  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  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
 18 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  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 17 26  1  0  0  0  0
 20 26  1  0  0  0  0
 14 27  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  2  0  0  0  0
 11 29  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
  5 32  1  0  0  0  0
 32 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
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304480

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2OC=C3C(CC4N(CCC5=C4NC4=CC=C(O)C=C54)C3=O)C2C=C)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30N2O9/c1-2-12-14-8-18-20-13(15-7-11(30)3-4-17(15)27-20)5-6-28(18)24(34)16(14)10-35-25(12)37-26-23(33)22(32)21(31)19(9-29)36-26/h2-4,7,10,12,14,18-19,21-23,25-27,29-33H,1,5-6,8-9H2

> <INCHI_KEY>
ZDYTVCFDZWEYRR-UHFFFAOYSA-N

> <FORMULA>
C26H30N2O9

> <MOLECULAR_WEIGHT>
514.531

> <EXACT_MASS>
514.195130554

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.11439000726172

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one

> <ALOGPS_LOGP>
0.28

> <JCHEM_LOGP>
-0.3286861133333321

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.207857319700514

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.552254141482749

> <JCHEM_PKA_STRONGEST_BASIC>
0.048932276362994576

> <JCHEM_POLAR_SURFACE_AREA>
164.94

> <JCHEM_REFRACTIVITY>
128.83180000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one

> <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  O   UNK     0      19.128  -3.037   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      17.615  -3.323   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.610  -2.157   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      15.097  -2.444   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      14.092  -1.277   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.579  -1.564   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.574  -0.397   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      12.082   1.057   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.077   2.224   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.564   1.937   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.056   0.483   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.543   0.196   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.538   1.363   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       7.046   2.817   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       6.041   3.984   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.527   3.697   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.019   2.243   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.025   1.076   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.225  -0.240   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       2.726   0.113   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.461  -0.765   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.068  -0.108   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.059   1.427   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.452   2.084   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.206   2.305   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.599   1.648   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.559   3.104   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.067   4.557   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.061  -0.684   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.553  -2.138   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.558  -3.304   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.600   0.177   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.595   1.344   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      16.113   0.464   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      16.621   1.918   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      17.118  -0.703   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      18.631  -0.416   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   27                                                  
CONECT   11   10   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   17   20                                                  
CONECT   27   14   10   28                                                  
CONECT   28   27                                                            
CONECT   29   11    7   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32    5   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    3   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀N₂O₉

Average Mass

514.5310 Da

Monoisotopic Mass

514.19513 Da

IUPAC Name

19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one

Traditional Name

19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2OC=C3C(CC4N(CCC5=C4NC4=CC=C(O)C=C54)C3=O)C2C=C)C(O)C(O)C1O

InChI Identifier

InChI=1S/C26H30N2O9/c1-2-12-14-8-18-20-13(15-7-11(30)3-4-17(15)27-20)5-6-28(18)24(34)16(14)10-35-25(12)37-26-23(33)22(32)21(31)19(9-29)36-26/h2-4,7,10,12,14,18-19,21-23,25-27,29-33H,1,5-6,8-9H2

InChI Key

ZDYTVCFDZWEYRR-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 sulfuric acid monoesters. These are organic compounds containing the sulfuric acid monoester functional group, with the generic structure ROS(O)(=O)=O, (R=organyl group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfuric acids and derivatives

Sub Class

Sulfuric acid esters

Direct Parent

Sulfuric acid monoesters

Alternative Parents

Substituents

Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	0.28	ALOGPS
logP	-0.33	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.55	ChemAxon
pKa (Strongest Basic)	0.049	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.94 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	128.83 m³·mol⁻¹	ChemAxon
Polarizability	53.11 Å³	ChemAxon
Number of Rings	6	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

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

77906992

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-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one (NP0304480)

MOL for NP0304480 (19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

3D MOL for NP0304480 (19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

3D SDF for NP0304480 (19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

3D-SDF for NP0304480 (19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

PDB for NP0304480 (19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

3D PDB for NP0304480 (19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

SMILES for NP0304480 (19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

INCHI for NP0304480 (19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

Structure for NP0304480 (19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

3D Structure for NP0304480 (19-ethenyl-7-hydroxy-18-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)