NP-MRD: Showing NP-Card for 3-Oxotirucalla-7,24-dien-21-oic acid (NP0083784)

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Record Information

Version

2.0

Created at

2022-04-29 04:43:20 UTC

Updated at

2022-04-29 04:43:20 UTC

NP-MRD ID

NP0083784

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Oxotirucalla-7,24-dien-21-oic acid

Description

3-Oxotirucalla-7,24-dien-21-oic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3-Oxotirucalla-7,24-dien-21-oic acid is found in Brucea javanica, Peganum harmala and Peganum nigellastrum. 3-Oxotirucalla-7,24-dien-21-oic acid was first documented in 2021 (PMID: 32011174). Based on a literature review a small amount of articles have been published on 3-oxotirucalla-7,24-dien-21-oic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206432D          

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M  END

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M  END


  Mrv1652304292206432D          

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  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  6  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
  9 13  1  1  0  0  0
  9 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
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  1  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
  2 34  1  0  0  0  0
  2 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0083784

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CC[C@]2(C)C3=CC[C@@]4([H])C(C)(C)C(=O)CC[C@]4(C)[C@@]3([H])CC[C@@]12C)[C@H](CCC=C(C)C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,11,20-22,24H,8,10,12-18H2,1-7H3,(H,32,33)/t20-,21-,22-,24-,28+,29-,30+/m0/s1

> <INCHI_KEY>
PYHNHGARAGBCRY-ZYHXIRFQSA-N

> <FORMULA>
C30H46O3

> <MOLECULAR_WEIGHT>
454.695

> <EXACT_MASS>
454.344695341

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.973305881245444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-6-methyl-2-[(1R,2R,7R,11S,14S,15S)-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]hept-5-enoic acid

> <ALOGPS_LOGP>
7.33

> <JCHEM_LOGP>
7.2495834683333324

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.91173349378445

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.851683133139874

> <JCHEM_PKA_STRONGEST_BASIC>
-7.471091142986859

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
135.6803

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-6-methyl-2-[(1R,2R,7R,11S,14S,15S)-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]hept-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       8.791   0.621   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0       6.466   0.217   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       2.388   3.656   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.200   5.313   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.764   0.984   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      -2.180   3.587   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.138   4.882   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.083   6.098   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.609   5.887   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.189   4.461   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.244   3.245   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -7.714   4.250   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.032   6.519   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.977   7.735   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.494   6.730   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.929  -0.051   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34   35                                             
CONECT    3    2    4    5   12                                             
CONECT    4    3                                                            
CONECT    5    3    6    8    9                                             
CONECT    6    5    7                                                       
CONECT    7    6   35                                                       
CONECT    8    5                                                            
CONECT    9    5   10   13   14                                             
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11    3                                                       
CONECT   13    9                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   22                                             
CONECT   17   16                                                            
CONECT   18   16   10   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   24   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    2                                                            
CONECT   35    2    7   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
3-Oxotirucalla-7,24-dien-21-Oate	Generator

Chemical Formula

C₃₀H₄₆O₃

Average Mass

454.6950 Da

Monoisotopic Mass

454.34470 Da

IUPAC Name

(2S)-6-methyl-2-[(1R,2R,7R,11S,14S,15S)-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]hept-5-enoic acid

Traditional Name

(2S)-6-methyl-2-[(1R,2R,7R,11S,14S,15S)-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]hept-5-enoic acid

CAS Registry Number

Not Available

SMILES

[H][C@]1(CC[C@]2(C)C3=CC[C@@]4([H])C(C)(C)C(=O)CC[C@]4(C)[C@@]3([H])CC[C@@]12C)[C@H](CCC=C(C)C)C(O)=O

InChI Identifier

InChI=1S/C30H46O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,11,20-22,24H,8,10,12-18H2,1-7H3,(H,32,33)/t20-,21-,22-,24-,28+,29-,30+/m0/s1

InChI Key

PYHNHGARAGBCRY-ZYHXIRFQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Brucea javanica	LOTUS Database	35616633
Peganum harmala	Plant	KNApSAcK
Peganum nigellastrum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cholesterol-skeleton
Cholestane-skeleton
Bile acid, alcohol, or derivatives
Steroid acid
3-oxo-delta-7-steroid
3-oxosteroid
3-oxo-5-alpha-steroid
Oxosteroid
Steroid
Delta-7-steroid
Medium-chain fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic ketone
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	7.33	ALOGPS
logP	7.25	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.85	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.68 m³·mol⁻¹	ChemAxon
Polarizability	54.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00052693

Chemspider ID

139103

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

158100

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Leutcha BP, Sema DK, Dzoyem JP, Ayimele GA, Nyongbela KD, Delie F, Alleman E, Sewald N, Meli Lannang A: Cytotoxicity of a new tirucallane derivative isolated from Stereospermum acuminatissimum K. Schum stem bark. Nat Prod Res. 2021 Nov;35(22):4417-4422. doi: 10.1080/14786419.2020.1723085. Epub 2020 Feb 3. [PubMed:32011174 ]

Showing NP-Card for 3-Oxotirucalla-7,24-dien-21-oic acid (NP0083784)

MOL for NP0083784 (3-Oxotirucalla-7,24-dien-21-oic acid)

3D MOL for NP0083784 (3-Oxotirucalla-7,24-dien-21-oic acid)

3D SDF for NP0083784 (3-Oxotirucalla-7,24-dien-21-oic acid)

3D-SDF for NP0083784 (3-Oxotirucalla-7,24-dien-21-oic acid)

PDB for NP0083784 (3-Oxotirucalla-7,24-dien-21-oic acid)

3D PDB for NP0083784 (3-Oxotirucalla-7,24-dien-21-oic acid)

SMILES for NP0083784 (3-Oxotirucalla-7,24-dien-21-oic acid)

INCHI for NP0083784 (3-Oxotirucalla-7,24-dien-21-oic acid)

Structure for NP0083784 (3-Oxotirucalla-7,24-dien-21-oic acid)

3D Structure for NP0083784 (3-Oxotirucalla-7,24-dien-21-oic acid)