NP-MRD: Showing NP-Card for 21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione (NP0280133)

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Record Information

Version

2.0

Created at

2022-09-09 05:45:46 UTC

Updated at

2022-09-09 05:45:46 UTC

NP-MRD ID

NP0280133

Secondary Accession Numbers

None

Natural Product Identification

Common Name

21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione

Description

21,25,28-Trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]Nonacosa-1(28),3,19,21-tetraene-2,29-dione belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. 21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione is found in Discodermia dissoluta. 21,25,28-Trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]Nonacosa-1(28),3,19,21-tetraene-2,29-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231521222D          

 35 40  0  0  0  0            999 V2000
   10.2135    0.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004231521222D          

 35 40  0  0  0  0            999 V2000
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 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 25  1  4  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
  6 32  1  0  0  0  0
 24 33  1  0  0  0  0
 21 33  1  0  0  0  0
 33 34  2  0  0  0  0
 23 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0280133

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2OC2C2CC3CC4CC=CC(=O)NCCC(O)C5NC(O)=C(C5=O)C(=O)C=CC4CC3C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H34N2O6/c1-12-21-16-10-14-5-6-18(30)22-24(33)23(29-27(22)34)19(31)7-8-28-20(32)4-2-3-13(14)9-15(16)11-17(21)26-25(12)35-26/h2,4-6,12-17,19,21,23,25-26,29,31,34H,3,7-11H2,1H3,(H,28,32)

> <INCHI_KEY>
QNUCYHJCXBLKDH-UHFFFAOYSA-N

> <FORMULA>
C27H34N2O6

> <MOLECULAR_WEIGHT>
482.577

> <EXACT_MASS>
482.241686823

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.32029511703465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
25,28-dihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19-triene-2,21,29-trione

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
2.1462011973333337

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.440674908531222

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7187955720738155

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15436714431212095

> <JCHEM_POLAR_SURFACE_AREA>
128.26

> <JCHEM_REFRACTIVITY>
139.2096

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
25,28-dihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19-triene-2,21,29-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      19.065   1.611   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.380   0.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.785  -0.527   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      22.028  -1.436   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      20.619  -2.058   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.112  -2.373   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.078  -3.515   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.673  -2.884   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.674  -4.015   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.021  -2.596   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.264  -3.506   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.098  -5.037   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.689  -5.658   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.446  -4.749   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.612  -3.218   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      11.038  -5.371   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       9.795  -4.462   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.386  -5.084   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.143  -4.175   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.734  -4.796   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.309  -2.644   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.408  -1.395   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       7.317  -0.152   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.883  -0.491   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.292   0.131   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.458   1.662   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.535  -0.778   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.944  -0.156   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.187  -1.065   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.596  -0.443   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.839  -1.353   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      18.346  -1.037   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.718  -2.022   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.961  -2.931   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       6.770   1.288   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3    5                                                       
CONECT    5    4    3    6                                                  
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   33                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   35                                                  
CONECT   24   23   25   33                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   10   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30    8   32                                                  
CONECT   32   31    2    6                                                  
CONECT   33   24   21   34                                                  
CONECT   34   33                                                            
CONECT   35   23                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄N₂O₆

Average Mass

482.5770 Da

Monoisotopic Mass

482.24169 Da

IUPAC Name

25,28-dihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19-triene-2,21,29-trione

Traditional Name

25,28-dihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19-triene-2,21,29-trione

CAS Registry Number

Not Available

SMILES

CC1C2OC2C2CC3CC4CC=CC(=O)NCCC(O)C5NC(O)=C(C5=O)C(=O)C=CC4CC3C12

InChI Identifier

InChI=1S/C27H34N2O6/c1-12-21-16-10-14-5-6-18(30)22-24(33)23(29-27(22)34)19(31)7-8-28-20(32)4-2-3-13(14)9-15(16)11-17(21)26-25(12)35-26/h2,4-6,12-17,19,21,23,25-26,29,31,34H,3,7-11H2,1H3,(H,28,32)

InChI Key

QNUCYHJCXBLKDH-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
Discodermia dissoluta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Oxane
Pyrroline
Cyclic carboximidic acid
Vinylogous acid
Vinylogous amide
Ketene acetal or derivatives
Ketone
Secondary alcohol
Dialkyl ether
Secondary aliphatic amine
Oxirane
Ether
Oxacycle
Azacycle
Polyol
Secondary amine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Alkanolamine
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Alcohol
Amine
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.24	ALOGPS
logP	2.15	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-0.15	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	128.26 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	139.21 m³·mol⁻¹	ChemAxon
Polarizability	51.32 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

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 21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione (NP0280133)

MOL for NP0280133 (21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione)

3D MOL for NP0280133 (21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione)

3D SDF for NP0280133 (21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione)

3D-SDF for NP0280133 (21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione)

PDB for NP0280133 (21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione)

3D PDB for NP0280133 (21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione)

SMILES for NP0280133 (21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione)

INCHI for NP0280133 (21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione)

Structure for NP0280133 (21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione)

3D Structure for NP0280133 (21,25,28-trihydroxy-9-methyl-11-oxa-22,27-diazahexacyclo[24.2.1.0⁵,¹⁷.0⁷,¹⁵.0⁸,¹³.0¹⁰,¹²]nonacosa-1(28),3,19,21-tetraene-2,29-dione)