NP-MRD: Showing NP-Card for (1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione (NP0147423)

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Record Information

Version

2.0

Created at

2022-09-02 03:01:26 UTC

Updated at

2022-09-02 03:01:26 UTC

NP-MRD ID

NP0147423

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione

Description

Norzoanthamine belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. (1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione was first documented in 2014 (PMID: 25317536). Based on a literature review a small amount of articles have been published on Norzoanthamine (PMID: 28496473) (PMID: 35033947) (PMID: 33822444) (PMID: 30036989).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022205012D          

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M  END

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 11 12  1  6  0  0  0
 11 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  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 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  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 25 32  1  1  0  0  0
 14 32  1  1  0  0  0
 30 33  1  6  0  0  0
 25 33  1  0  0  0  0
 11 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  6  0  0  0
  2 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147423

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@@H]2CN3[C@](CC[C@@]4(C)[C@]5(C)CC(=O)O[C@@]34C[C@@]3(C)[C@@H]4CC(C)=CC(=O)[C@H]4CC(=O)[C@H]53)(C1)O2

> <INCHI_IDENTIFIER>
InChI=1S/C29H39NO5/c1-16-9-20-19(21(31)10-16)11-22(32)24-25(20,3)15-29-27(5,26(24,4)13-23(33)35-29)6-7-28-12-17(2)8-18(34-28)14-30(28)29/h10,17-20,24H,6-9,11-15H2,1-5H3/t17-,18+,19-,20+,24-,25-,26+,27-,28-,29+/m0/s1

> <INCHI_KEY>
RNNGFZNWONBXEI-RRSOKNRKSA-N

> <FORMULA>
C29H39NO5

> <MOLECULAR_WEIGHT>
481.633

> <EXACT_MASS>
481.28282336

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
37.068665828183704

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,4R,9S,12S,13R,14S,17S,19S,21R)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1^{17,21}.0^{1,14}.0^{3,12}.0^{4,9}.0^{17,23}]heptacos-6-ene-8,11,25-trione

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
4.435992178333333

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.89135937304019

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.709542225357694

> <JCHEM_PKA_STRONGEST_BASIC>
2.0917524047788585

> <JCHEM_POLAR_SURFACE_AREA>
72.91000000000001

> <JCHEM_REFRACTIVITY>
130.7973

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4R,9S,12S,13R,14S,17S,19S,21R)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1^{17,21}.0^{1,14}.0^{3,12}.0^{4,9}.0^{17,23}]heptacos-6-ene-8,11,25-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.952   2.481   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.460   2.991   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.586   4.526   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.978   5.184   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.937   6.803   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.244   4.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.637   4.966   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.903   4.089   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.056   5.236   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.777   2.554   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.164   2.272   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.091   0.861   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.865   0.446   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.523  -0.946   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.973  -1.465   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.365  -0.807   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.804  -1.717   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.884   0.643   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.226   2.035   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.625   2.868   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.502   0.882   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.418  -0.355   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.461   1.752   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.922   1.772   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.125   0.415   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.894   1.515   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.358   1.073   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.888   2.220   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.102  -0.510   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.329  -1.600   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.838  -2.231   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       5.961  -1.012   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0       4.159  -0.552   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.118   2.773   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.726   2.115   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   19                                                  
CONECT   11   10   12   13   34                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   21   32                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   10   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   14   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   32   33                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31   25   14                                                  
CONECT   33   30   25                                                       
CONECT   34   11    6   35                                                  
CONECT   35   34    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Value	Source
Norzoanthamine hydrochloride	MeSH

Chemical Formula

C₂₉H₃₉NO₅

Average Mass

481.6330 Da

Monoisotopic Mass

481.28282 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@H]2CN3[C@](CC[C@@]4(C)[C@]5(C)CC(=O)O[C@@]34C[C@@]3(C)[C@@H]4CC(C)=CC(=O)[C@H]4CC(=O)[C@H]53)(C1)O2

InChI Identifier

InChI=1S/C29H39NO5/c1-16-9-20-19(21(31)10-16)11-22(32)24-25(20,3)15-29-27(5,26(24,4)13-23(33)35-29)6-7-28-12-17(2)8-18(34-28)14-30(28)29/h10,17-20,24H,6-9,11-15H2,1-5H3/t17-,18+,19-,20+,24-,25-,26+,27-,28-,29+/m0/s1

InChI Key

RNNGFZNWONBXEI-RRSOKNRKSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Azaspirodecane
Quinolidine
Azepane
Cyclohexenone
Delta valerolactone
Delta_valerolactone
Piperidine
Oxane
Oxazolidine
Carboxylic acid ester
Hemiaminal
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
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	2.86	ALOGPS
logS	-4.5	ALOGPS

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

Norzoanthamine

METLIN ID

Not Available

PubChem Compound

24939455

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Farrokhnia M, Mahnam K: Molecular Dynamics and Docking Investigations of Several Zoanthamine-Type Marine Alkaloids as Matrix Metaloproteinase-1 Inhibitors. Iran J Pharm Res. 2017 Winter;16(1):173-186. [PubMed:28496473 ]
Garcia-Garcia P, Reyes R, Evora C, Delgado A, Fernandez JJ, Daranas AH: Osteoprotective effect of the marine alkaloid norzoanthamine on an osteoporosis model in ovariectomized rat. Biomed Pharmacother. 2022 Mar;147:112631. doi: 10.1016/j.biopha.2022.112631. Epub 2022 Jan 13. [PubMed:35033947 ]
Xin Z, Wang H, He H, Zhao X, Gao S: Asymmetric Total Synthesis of Norzoanthamine. Angew Chem Int Ed Engl. 2021 Jun 1;60(23):12807-12812. doi: 10.1002/anie.202102643. Epub 2021 May 5. [PubMed:33822444 ]
Guillen PO, Gegunde S, Jaramillo KB, Alfonso A, Calabro K, Alonso E, Rodriguez J, Botana LM, Thomas OP: Zoanthamine Alkaloids from the Zoantharian Zoanthus cf. pulchellus and Their Effects in Neuroinflammation. Mar Drugs. 2018 Jul 20;16(7):242. doi: 10.3390/md16070242. [PubMed:30036989 ]
Cen-Pacheco F, Martin MN, Fernandez JJ, Hernandez Daranas A: New oxidized zoanthamines from a Canary Islands Zoanthus sp. Mar Drugs. 2014 Oct 14;12(10):5188-96. doi: 10.3390/md12105188. [PubMed:25317536 ]
LOTUS database [Link]

Showing NP-Card for (1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione (NP0147423)

MOL for NP0147423 ((1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione)

3D MOL for NP0147423 ((1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione)

3D SDF for NP0147423 ((1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione)

3D-SDF for NP0147423 ((1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione)

PDB for NP0147423 ((1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione)

3D PDB for NP0147423 ((1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione)

SMILES for NP0147423 ((1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione)

INCHI for NP0147423 ((1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione)

Structure for NP0147423 ((1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione)

3D Structure for NP0147423 ((1r,3s,4r,9s,12s,13r,14s,17s,19s,21r)-3,6,13,14,19-pentamethyl-24,27-dioxa-23-azaheptacyclo[11.10.3.1¹⁷,²¹.0¹,¹⁴.0³,¹².0⁴,⁹.0¹⁷,²³]heptacos-6-ene-8,11,25-trione)