NP-MRD: Showing NP-Card for (1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol (NP0278664)

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Record Information

Version

2.0

Created at

2022-09-09 03:46:19 UTC

Updated at

2022-09-09 03:46:19 UTC

NP-MRD ID

NP0278664

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol

Description

(+)-Araguspongine C belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms. (1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol is found in Neopetrosia chaliniformis. (1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol was first documented in 2002 (PMID: 12502314). Based on a literature review a small amount of articles have been published on (+)-Araguspongine C (PMID: 26978377) (PMID: 25580621) (PMID: 29595068).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092205462D          

 34 38  0  0  1  0            999 V2000
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    8.6621   -0.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8385   -0.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 16 33  1  0  0  0  0
 12 33  1  0  0  0  0
 33 34  1  6  0  0  0
  9 34  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309092205462D          

 34 38  0  0  1  0            999 V2000
   11.2142    1.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9224    2.1244    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   11.7295    3.3036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4103    2.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3471    2.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6031    1.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9856    2.9470    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3048    3.4130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8136    2.0150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4944    1.5490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
 27 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  6  0  0  0
 24 32  1  6  0  0  0
 16 33  1  0  0  0  0
 12 33  1  0  0  0  0
 33 34  1  6  0  0  0
  9 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0278664

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@]12CCCN3CC[C@@H](CCCCCC[C@@]4(O)CCCN5CC[C@@H](CCCCCC1)O[C@@H]45)O[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C28H50N2O4/c31-27-15-7-3-1-5-11-23-13-21-29-20-10-18-28(32,26(29)33-23)16-8-4-2-6-12-24-14-22-30(19-9-17-27)25(27)34-24/h23-26,31-32H,1-22H2/t23-,24-,25+,26+,27-,28-/m1/s1

> <INCHI_KEY>
XBUGUOQUMLNGNN-BNNSEFEDSA-N

> <FORMULA>
C28H50N2O4

> <MOLECULAR_WEIGHT>
478.718

> <EXACT_MASS>
478.377058098

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
56.62500502204841

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,8R,10S,15R,22R,29S)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2^{8,11}.0^{10,15}.0^{25,29}]dotriacontane-1,15-diol

> <JCHEM_LOGP>
4.601154516666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
13.751234771213564

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.14917516117967

> <JCHEM_PKA_STRONGEST_BASIC>
7.393680330099281

> <JCHEM_POLAR_SURFACE_AREA>
65.4

> <JCHEM_REFRACTIVITY>
135.3478

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8R,10S,15R,22R,29S)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2^{8,11}.0^{10,15}.0^{25,29}]dotriacontane-1,15-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0      20.933   2.525   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      20.388   3.966   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.930   2.149   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.955   0.957   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.659   0.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.169  -0.267   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.632  -0.178   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.197   0.381   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.005   1.356   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.616   0.690   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.345   1.560   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       9.463   3.096   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       8.193   3.966   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.311   5.501   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.699   6.167   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.970   5.297   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.425   6.737   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.429   7.114   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.404   8.305   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.700   9.138   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.189   9.529   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.727   9.441   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.162   8.882   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.354   7.906   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.742   8.572   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.013   7.702   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      21.895   6.167   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      23.166   5.297   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      23.048   3.761   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      21.659   3.096   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.506   5.501   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      19.236   6.371   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.852   3.761   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.123   2.891   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30   31                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   34                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   33                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    2                                                       
CONECT   31   27    2   32                                                  
CONECT   32   31   24                                                       
CONECT   33   16   12   34                                                  
CONECT   34   33    9                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Araguspongine C	MeSH

Chemical Formula

C₂₈H₅₀N₂O₄

Average Mass

478.7180 Da

Monoisotopic Mass

478.37706 Da

IUPAC Name

(1R,8R,10S,15R,22R,29S)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2^{8,11}.0^{10,15}.0^{25,29}]dotriacontane-1,15-diol

Traditional Name

(1R,8R,10S,15R,22R,29S)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2^{8,11}.0^{10,15}.0^{25,29}]dotriacontane-1,15-diol

CAS Registry Number

Not Available

SMILES

O[C@@]12CCCN3CC[C@@H](CCCCCC[C@@]4(O)CCCN5CC[C@@H](CCCCCC1)O[C@@H]45)O[C@@H]23

InChI Identifier

InChI=1S/C28H50N2O4/c31-27-15-7-3-1-5-11-23-13-21-29-20-10-18-28(32,26(29)33-23)16-8-4-2-6-12-24-14-22-30(19-9-17-27)25(27)34-24/h23-26,31-32H,1-22H2/t23-,24-,25+,26+,27-,28-/m1/s1

InChI Key

XBUGUOQUMLNGNN-BNNSEFEDSA-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
Neopetrosia chaliniformis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Not Available

Direct Parent

Piperidines

Alternative Parents

Substituents

Piperidine
Oxazinane
1,3-oxazinane
Tertiary alcohol
Hemiaminal
Oxacycle
Azacycle
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
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	4.6	ChemAxon
pKa (Strongest Acidic)	13.15	ChemAxon
pKa (Strongest Basic)	7.39	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.4 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	135.35 m³·mol⁻¹	ChemAxon
Polarizability	56.63 Å³	ChemAxon
Number of Rings	5	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

4440686

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5276744

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ebrahim HY, El Sayed KA: Discovery of Novel Antiangiogenic Marine Natural Product Scaffolds. Mar Drugs. 2016 Mar 11;14(3). pii: md14030057. doi: 10.3390/md14030057. [PubMed:26978377 ]
Akl MR, Ayoub NM, Ebrahim HY, Mohyeldin MM, Orabi KY, Foudah AI, El Sayed KA: Araguspongine C induces autophagic death in breast cancer cells through suppression of c-Met and HER2 receptor tyrosine kinase signaling. Mar Drugs. 2015 Jan 8;13(1):288-311. doi: 10.3390/md13010288. [PubMed:25580621 ]
Orabi KY, El Sayed KA, Hamann MT, Dunbar DC, Al-Said MS, Higa T, Kelly M: Araguspongines K and L, new bioactive bis-1-oxaquinolizidine N-oxide alkaloids from Red Sea specimens of Xestospongia exigua. J Nat Prod. 2002 Dec;65(12):1782-5. doi: 10.1021/np0202226. [PubMed:12502314 ]
Dung DT, Hang DTT, Yen PH, Quang TH, Nhiem NX, Tai BH, Minh CV, Kim YC, Kim DC, Oh H, Kiem PV: Macrocyclic bis-quinolizidine alkaloids from Xestospongia muta. Nat Prod Res. 2019 Feb;33(3):400-406. doi: 10.1080/14786419.2018.1455043. Epub 2018 Mar 29. [PubMed:29595068 ]
LOTUS database [Link]

Showing NP-Card for (1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol (NP0278664)

MOL for NP0278664 ((1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol)

3D MOL for NP0278664 ((1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol)

3D SDF for NP0278664 ((1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol)

3D-SDF for NP0278664 ((1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol)

PDB for NP0278664 ((1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol)

3D PDB for NP0278664 ((1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol)

SMILES for NP0278664 ((1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol)

INCHI for NP0278664 ((1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol)

Structure for NP0278664 ((1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol)

3D Structure for NP0278664 ((1r,8r,10s,15r,22r,29s)-9,30-dioxa-11,25-diazapentacyclo[20.6.2.2⁸,¹¹.0¹⁰,¹⁵.0²⁵,²⁹]dotriacontane-1,15-diol)