NP-MRD: Showing NP-Card for 10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one (NP0218525)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 19:13:06 UTC

Updated at

2022-09-05 19:13:06 UTC

NP-MRD ID

NP0218525

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one

Description

10,16,19-Trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-3-one belongs to the class of organic compounds known as hetisine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetisine skeleton, which is a heptacyclic compound with an additional N-C-6 bond as compared with the hetidine-type, and thus, is one of most complex entries in the atisane-class. 10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one is found in Delphinium occidentale. Based on a literature review very few articles have been published on 10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-3-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052221132D          

 25 31  0  0  0  0            999 V2000
   -1.1906    0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845    0.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    0.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203    0.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9611    1.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7940    0.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838    1.2844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4176   -0.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0434   -0.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4083   -1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8224   -0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3560    0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254    1.0787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4804    0.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5733    0.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890   -0.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2832   -0.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6437   -0.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6973   -1.7584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0301   -0.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342   -0.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7014    0.7890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    0.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546   -0.3506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3006   -1.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  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
  6  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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  4 23  1  0  0  0  0
 15 23  1  0  0  0  0
 16 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 25  1  0  0  0  0
M  END


  Mrv1652309052221132D          

 25 31  0  0  0  0            999 V2000
   -1.1906    0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845    0.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    0.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203    0.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9611    1.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7940    0.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838    1.2844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4176   -0.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0434   -0.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4083   -1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8224   -0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3560    0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254    1.0787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4804    0.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5733    0.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890   -0.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2832   -0.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6437   -0.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6973   -1.7584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0301   -0.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342   -0.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7014    0.7890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6811    0.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546   -0.3506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3006   -1.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  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
  6  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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  4 23  1  0  0  0  0
 15 23  1  0  0  0  0
 16 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218525

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CN3C4C5C(O)C6C(O)C7C5(CC6=C)CC3(O)C1C47CC(=O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H25NO4/c1-8-3-18-6-20(25)16-17(2)4-9(22)5-19(16)14(18)13(24)10(8)12(23)11(18)15(19)21(20)7-17/h10-16,23-25H,1,3-7H2,2H3

> <INCHI_KEY>
PMNKYICLUOJFEE-UHFFFAOYSA-N

> <FORMULA>
C20H25NO4

> <MOLECULAR_WEIGHT>
343.423

> <EXACT_MASS>
343.178358289

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.145186804959025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-one

> <JCHEM_LOGP>
-1.2480000310000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.209582998854817

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.925602281873907

> <JCHEM_PKA_STRONGEST_BASIC>
7.060584231085891

> <JCHEM_POLAR_SURFACE_AREA>
81.0

> <JCHEM_REFRACTIVITY>
89.0634

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.223   0.896   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.718   0.568   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.494   1.597   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.091   1.185   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.661   1.913   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.216   1.158   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.130   2.398   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.379  -0.088   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.548  -1.271   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.229  -2.652   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.002  -0.619   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.131   0.747   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.007   2.014   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.497   1.091   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.803   0.273   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.900  -1.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.395  -0.629   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.202  -1.746   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.302  -3.282   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.056  -0.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.370  -0.066   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.309   1.473   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.138   0.309   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       5.329  -0.655   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       6.161  -2.019   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17   23                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8   24                                             
CONECT    7    6                                                            
CONECT    8    6    9   15                                                  
CONECT    9    8   10   11   25                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    8   16   23                                             
CONECT   16   15   17   24                                                  
CONECT   17   16    4   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    2   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    4   15                                                  
CONECT   24   16    6   25                                                  
CONECT   25   24    9                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₅NO₄

Average Mass

343.4230 Da

Monoisotopic Mass

343.17836 Da

IUPAC Name

10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-one

Traditional Name

10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-one

CAS Registry Number

Not Available

SMILES

CC12CN3C4C5C(O)C6C(O)C7C5(CC6=C)CC3(O)C1C47CC(=O)C2

InChI Identifier

InChI=1S/C20H25NO4/c1-8-3-18-6-20(25)16-17(2)4-9(22)5-19(16)14(18)13(24)10(8)12(23)11(18)15(19)21(20)7-17/h10-16,23-25H,1,3-7H2,2H3

InChI Key

PMNKYICLUOJFEE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Delphinium occidentale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hetisine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetisine skeleton, which is a heptacyclic compound with an additional N-C-6 bond as compared with the hetidine-type, and thus, is one of most complex entries in the atisane-class.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Hetisine-type diterpenoid alkaloids

Alternative Parents

Substituents

Hetisine-type diterpenoid alkaloid
Azaspirodecane
Isoindolone
Quinolizidine
Indole or derivatives
Indolizidine
Isoindoline
Isoindole or derivatives
Alkaloid or derivatives
Azepane
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Hemiaminal
Polyol
Alkanolamine
Organoheterocyclic compound
Azacycle
Alcohol
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organooxygen 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	-1.2	ChemAxon
pKa (Strongest Acidic)	12.93	ChemAxon
pKa (Strongest Basic)	7.06	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.06 m³·mol⁻¹	ChemAxon
Polarizability	36.15 Å³	ChemAxon
Number of Rings	7	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

163105534

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one (NP0218525)

MOL for NP0218525 (10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

3D MOL for NP0218525 (10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

3D SDF for NP0218525 (10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

3D-SDF for NP0218525 (10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

PDB for NP0218525 (10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

3D PDB for NP0218525 (10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

SMILES for NP0218525 (10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

INCHI for NP0218525 (10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

Structure for NP0218525 (10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)

3D Structure for NP0218525 (10,16,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-one)