NP-MRD: Showing NP-Card for 3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate (NP0190888)

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Record Information

Version

2.0

Created at

2022-09-04 07:38:29 UTC

Updated at

2022-09-04 07:38:29 UTC

NP-MRD ID

NP0190888

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate

Description

3,19-Dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-10-yl 3-phenylprop-2-enoate belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. 3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate is found in Aconitum palmatum. 3,19-Dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-10-yl 3-phenylprop-2-enoate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241507252D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004241507252D          

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  9 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
  2 29  1  0  0  0  0
  7 29  1  0  0  0  0
 28 30  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 31  1  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 22 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0190888

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CN3C4CC56CC(=C)C7C(O)C5C(CC(O)C1)(C3C6C7OC(=O)C=CC1=CC=CC=C1)C24

> <INCHI_IDENTIFIER>
InChI=1S/C29H33NO4/c1-15-10-28-13-18-24-27(2)11-17(31)12-29(24)25(28)22(33)20(15)23(21(28)26(29)30(18)14-27)34-19(32)9-8-16-6-4-3-5-7-16/h3-9,17-18,20-26,31,33H,1,10-14H2,2H3

> <INCHI_KEY>
JZBNMSVUZKTTOR-UHFFFAOYSA-N

> <FORMULA>
C29H33NO4

> <MOLECULAR_WEIGHT>
459.586

> <EXACT_MASS>
459.240958547

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.3027480479056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
2.1111261259999985

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.296335532465957

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.428785578911505

> <JCHEM_PKA_STRONGEST_BASIC>
9.067172600334642

> <JCHEM_POLAR_SURFACE_AREA>
70.0

> <JCHEM_REFRACTIVITY>
128.02630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.705  -4.278   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.012  -3.464   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.169  -2.184   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.919  -0.815   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.079   0.476   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.456  -0.686   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.431  -2.044   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.269  -3.496   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.254  -3.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.823  -2.979   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.113  -3.820   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.487  -3.123   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.570  -1.585   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.777  -3.964   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.150  -3.267   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.440  -4.108   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.814  -3.411   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.104  -4.253   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.020  -5.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.647  -6.487   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.357  -5.646   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.848  -1.372   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.193  -0.561   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.049   0.972   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.840  -1.576   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.542  -2.983   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.044  -4.583   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.427  -4.538   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.653  -3.532   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       3.412  -2.856   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       2.747  -4.716   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.794  -1.377   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.093  -0.315   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.297   1.212   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29   31                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   25   29                                             
CONECT    8    7    9   30                                                  
CONECT    9    8   10   26                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   10   23   33                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    7   26                                                  
CONECT   26   25    9   27   32                                             
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28    2    7                                                  
CONECT   30   28    8   31                                                  
CONECT   31   30    2                                                       
CONECT   32   26   33                                                       
CONECT   33   32   22   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   82    0
END

View in JSmol

Synonyms

Value	Source
3,19-Dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0,.0,.0,.0,.0,]nonadecan-10-yl 3-phenylprop-2-enoic acid	Generator
3,19-Dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₂₉H₃₃NO₄

Average Mass

459.5860 Da

Monoisotopic Mass

459.24096 Da

IUPAC Name

3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate

Traditional Name

3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC12CN3C4CC56CC(=C)C7C(O)C5C(CC(O)C1)(C3C6C7OC(=O)C=CC1=CC=CC=C1)C24

InChI Identifier

InChI=1S/C29H33NO4/c1-15-10-28-13-18-24-27(2)11-17(31)12-29(24)25(28)22(33)20(15)23(21(28)26(29)30(18)14-27)34-19(32)9-8-16-6-4-3-5-7-16/h3-9,17-18,20-26,31,33H,1,10-14H2,2H3

InChI Key

JZBNMSVUZKTTOR-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
Aconitum palmatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Cinnamic acid ester
Cinnamic acid or derivatives
Azaspirodecane
Quinolizidine
Isoindole or derivatives
Isoindoline
Indolizidine
Indole or derivatives
Alkaloid or derivatives
Styrene
Azepane
Fatty acid ester
Piperidine
Monocyclic benzene moiety
Benzenoid
Fatty acyl
N-alkylpyrrolidine
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrrolidine
Secondary alcohol
Tertiary aliphatic amine
Amino acid or derivatives
Tertiary amine
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Amine
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	1.69	ALOGPS
logP	2.11	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	14.43	ChemAxon
pKa (Strongest Basic)	9.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	128.03 m³·mol⁻¹	ChemAxon
Polarizability	50.3 Å³	ChemAxon
Number of Rings	8	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

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 3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate (NP0190888)

MOL for NP0190888 (3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate)

3D MOL for NP0190888 (3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate)

3D SDF for NP0190888 (3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate)

3D-SDF for NP0190888 (3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate)

PDB for NP0190888 (3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate)

3D PDB for NP0190888 (3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate)

SMILES for NP0190888 (3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate)

INCHI for NP0190888 (3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate)

Structure for NP0190888 (3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate)

3D Structure for NP0190888 (3,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-10-yl 3-phenylprop-2-enoate)