NP-MRD: Showing NP-Card for (1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol (NP0162581)

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Record Information

Version

2.0

Created at

2022-09-02 21:00:45 UTC

Updated at

2022-09-02 21:00:45 UTC

NP-MRD ID

NP0162581

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol

Description

Chlidanthine belongs to the class of organic compounds known as galanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids with a structure characterized a tetracyclic skeleton with two ortho aromatic protons in ring A. (1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol is found in Chlidanthus fragrans and Hippeastrum puniceum. (1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol was first documented in 2011 (PMID: 21615016). Based on a literature review a small amount of articles have been published on Chlidanthine (PMID: 33578992) (PMID: 29433685) (PMID: 22086403).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022223002D          

 21 24  0  0  1  0            999 V2000
    3.5939    1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372    0.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5299    0.5753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2732   -0.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4659   -0.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9152    0.2357    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8873   -0.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8276   -1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826   -1.9049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1124   -2.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3991   -1.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -0.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2698   -0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5230    0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9696    1.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229    1.9812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630    1.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0902    0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5055    1.5062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1718    1.0198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9792    1.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
  6 18  1  1  0  0  0
 17 19  1  0  0  0  0
 20 19  1  1  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0162581

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@@H]2OC3=C4C(CN(C)CC[C@@]24C=C1)=CC=C3O

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO3/c1-18-8-7-17-6-5-12(20-2)9-14(17)21-16-13(19)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m0/s1

> <INCHI_KEY>
LPCKPBWOSNVCEL-JDFRZJQESA-N

> <FORMULA>
C17H21NO3

> <MOLECULAR_WEIGHT>
287.359

> <EXACT_MASS>
287.15214354

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.887978862117766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12S,14R)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17),15-tetraen-9-ol

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
1.4231386756508742

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.868834293745659

> <JCHEM_PKA_STRONGEST_BASIC>
8.513885638363744

> <JCHEM_POLAR_SURFACE_AREA>
41.93000000000001

> <JCHEM_REFRACTIVITY>
82.5738

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12S,14R)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17),15-tetraen-9-ol

> <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       6.709   2.854   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.229   1.391   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.722   1.074   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.243  -0.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.736  -0.707   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.708   0.440   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.656  -1.224   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.545  -2.828   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.154  -3.556   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.210  -5.052   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.745  -2.273   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.794  -0.759   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.370  -0.375   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.843   1.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.810   2.233   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.283   3.698   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.304   1.909   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.168   0.443   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.944   2.812   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.187   1.904   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.694   2.221   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   18   20                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17   12    6                                                  
CONECT   19   17   20                                                       
CONECT   20   19    6   21                                                  
CONECT   21   20    3                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₁NO₃

Average Mass

287.3590 Da

Monoisotopic Mass

287.15214 Da

IUPAC Name

(1S,12S,14R)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17),15-tetraen-9-ol

Traditional Name

(1S,12S,14R)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17),15-tetraen-9-ol

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@@H]2OC3=C4C(CN(C)CC[C@@]24C=C1)=CC=C3O

InChI Identifier

InChI=1S/C17H21NO3/c1-18-8-7-17-6-5-12(20-2)9-14(17)21-16-13(19)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m0/s1

InChI Key

LPCKPBWOSNVCEL-JDFRZJQESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chlidanthus fragrans	LOTUS Database	35616633
Hippeastrum puniceum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as galanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids with a structure characterized a tetracyclic skeleton with two ortho aromatic protons in ring A.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Galanthamine-type amaryllidaceae alkaloids

Direct Parent

Galanthamine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Galanthamine-type amaryllidaceae alkaloid
Benzazepine
Coumaran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Azepine
Phenol
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Dialkyl ether
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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	1.66	ALOGPS
logP	1.42	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	8.51	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.93 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	82.57 m³·mol⁻¹	ChemAxon
Polarizability	30.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

7990197

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9814447

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Spina R, Saliba S, Dupire F, Ptak A, Hehn A, Piutti S, Poinsignon S, Leclerc S, Bouguet-Bonnet S, Laurain-Mattar D: Molecular Identification of Endophytic Bacteria in Leucojum aestivum In Vitro Culture, NMR-Based Metabolomics Study and LC-MS Analysis Leading to Potential Amaryllidaceae Alkaloid Production. Int J Mol Sci. 2021 Feb 10;22(4). pii: ijms22041773. doi: 10.3390/ijms22041773. [PubMed:33578992 ]
Cahlikova L, Macakova K, Zavadil S, Jiros P, Opletal L, Urbanova K, Jahodar L: Analysis of Amaryllidaceae alkaloids from Chlidanthus fragrans by GC-MS and their cholinesterase activity. Nat Prod Commun. 2011 May;6(5):603-6. [PubMed:21615016 ]
Ortiz JE, Garro A, Pigni NB, Aguero MB, Roitman G, Slanis A, Enriz RD, Feresin GE, Bastida J, Tapia A: Cholinesterase-inhibitory effect and in silico analysis of alkaloids from bulbs of Hieronymiella species. Phytomedicine. 2018 Jan 15;39:66-74. doi: 10.1016/j.phymed.2017.12.020. Epub 2017 Dec 20. [PubMed:29433685 ]
Reyes-Chilpa R, Berkov S, Hernandez-Ortega S, Jankowski CK, Arseneau S, Clotet-Codina I, Este JA, Codina C, Viladomat F, Bastida J: Acetylcholinesterase-inhibiting alkaloids from Zephyranthes concolor. Molecules. 2011 Nov 15;16(11):9520-33. doi: 10.3390/molecules16119520. [PubMed:22086403 ]
LOTUS database [Link]

Showing NP-Card for (1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol (NP0162581)

MOL for NP0162581 ((1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol)

3D MOL for NP0162581 ((1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol)

3D SDF for NP0162581 ((1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol)

3D-SDF for NP0162581 ((1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol)

PDB for NP0162581 ((1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol)

3D PDB for NP0162581 ((1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol)

SMILES for NP0162581 ((1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol)

INCHI for NP0162581 ((1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol)

Structure for NP0162581 ((1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol)

3D Structure for NP0162581 ((1s,12s,14r)-14-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]heptadeca-6,8,10(17),15-tetraen-9-ol)