NP-MRD: Showing NP-Card for Cabralealactone (NP0076286)

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Record Information

Version

2.0

Created at

2022-04-28 21:26:07 UTC

Updated at

2022-04-28 21:26:07 UTC

NP-MRD ID

NP0076286

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cabralealactone

Description

Cabralealactone belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Cabralealactone is found in Aglaia abbreviata, Aglaia leucophylla, Aglaia tomentosa , Betula pendula, Cabralea eichleriana, Cabralea polytricha, Cleome africana and Dysoxylum cauliflorum. Cabralealactone was first documented in 2012 (PMID: 22803367). Based on a literature review a small amount of articles have been published on cabralealactone (PMID: 32536210) (PMID: 29872266) (PMID: 23659170).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223262D          

 30 34  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8 15  1  6  0  0  0
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M  END

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
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   -4.9534   -1.0162   -2.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4843   -1.3883   -3.2275 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8978    2.1973    0.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5940   -2.2444    0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282223262D          

 30 34  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8792   -0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076286

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(CCC(=O)O1)[C@H]1CC[C@]2(C)[C@@H]1CC[C@@H]1[C@@]3(C)CCC(=O)C(C)(C)[C@@H]3CC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O3/c1-23(2)19-10-15-26(5)20(24(19,3)13-11-21(23)28)8-7-17-18(9-14-25(17,26)4)27(6)16-12-22(29)30-27/h17-20H,7-16H2,1-6H3/t17-,18+,19+,20-,24+,25-,26-,27+/m1/s1

> <INCHI_KEY>
NOLGXQBEFHYZHI-QPBHWVAKSA-N

> <FORMULA>
C27H42O3

> <MOLECULAR_WEIGHT>
414.63

> <EXACT_MASS>
414.313395212

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
49.26986217441189

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-5-methyl-5-[(1R,2R,7R,10R,11R,14S,15R)-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]oxolan-2-one

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
5.977882722333334

> <ALOGPS_LOGS>
-6.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.962170441608716

> <JCHEM_PKA_STRONGEST_BASIC>
-6.91138120256236

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
118.39369999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.28e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-methyl-5-[(1R,2R,7R,10R,11R,14S,15R)-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.284   6.479   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.810   6.268   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.877   7.378   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.081   4.752   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.723   4.026   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.304   5.906   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.764   0.984   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.331   0.781   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.241  -0.130   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.601   0.361   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   29   30                                             
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8   28                                             
CONECT    7    6    1                                                       
CONECT    8    6    9   15                                                  
CONECT    9    8   10   12   27                                             
CONECT   10    9   11                                                       
CONECT   11   10    5                                                       
CONECT   12    9   13   18   26                                             
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14    8                                                       
CONECT   16   13   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   12                                                       
CONECT   19   16   20   24   25                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   19                                                       
CONECT   25   19                                                            
CONECT   26   12                                                            
CONECT   27    9                                                            
CONECT   28    6                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
(20S)-23,24-Epoxy-25,26,27-trinordammarane-3,24-dione	ChEBI

Chemical Formula

C₂₇H₄₂O₃

Average Mass

414.6300 Da

Monoisotopic Mass

414.31340 Da

IUPAC Name

(5S)-5-methyl-5-[(1R,2R,7R,10R,11R,14S,15R)-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]oxolan-2-one

Traditional Name

(5S)-5-methyl-5-[(1R,2R,7R,10R,11R,14S,15R)-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

C[C@]1(CCC(=O)O1)[C@H]1CC[C@]2(C)[C@@H]1CC[C@@H]1[C@@]3(C)CCC(=O)C(C)(C)[C@@H]3CC[C@@]21C

InChI Identifier

InChI=1S/C27H42O3/c1-23(2)19-10-15-26(5)20(24(19,3)13-11-21(23)28)8-7-17-18(9-14-25(17,26)4)27(6)16-12-22(29)30-27/h17-20H,7-16H2,1-6H3/t17-,18+,19+,20-,24+,25-,26-,27+/m1/s1

InChI Key

NOLGXQBEFHYZHI-QPBHWVAKSA-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
Aglaia abbreviata	LOTUS Database	35616633
Aglaia leucophylla	LOTUS Database	35616633
Aglaia tomentosa	Plant	KNApSAcK
Betula pendula	LOTUS Database	35616633
Cabralea eichleriana	-	KNApSAcK
Cabralea polytricha	-	KNApSAcK
Cleome africana	LOTUS Database	35616633
Dysoxylum cauliflorum	LOTUS Database	35616633

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
Steroid lactone
3-oxosteroid
Oxosteroid
14-alpha-methylsteroid
3-oxo-5-alpha-steroid
Steroid
Gamma butyrolactone
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

gamma-lactone (CHEBI:70268 )
tetracyclic triterpenoid (CHEBI:70268 )
cyclic terpene ketone (CHEBI:70268 )

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	5.35	ALOGPS
logP	5.98	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	19.96	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	118.39 m³·mol⁻¹	ChemAxon
Polarizability	49.27 Å³	ChemAxon
Number of Rings	5	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

C00038675

Chemspider ID

23281688

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44421647

PDB ID

Not Available

ChEBI ID

70268

Good Scents ID

Not Available

References

General References

Hutagaol RP, Harneti D, Safari A, Hidayat AT, Supratman U, Awang K, Shiono Y: Cytotoxic triterpenoids from the stem bark of Aglaia angustifolia. J Asian Nat Prod Res. 2021 Aug;23(8):781-788. doi: 10.1080/10286020.2020.1776704. Epub 2020 Jun 13. [PubMed:32536210 ]
Malik A, Arooj M, Butt TT, Zahid S, Zahid F, Jafar TH, Waquar S, Gan SH, Ahmad S, Mirza MU: In silico and in vivo characterization of cabralealactone, solasodin and salvadorin in a rat model: potential anti-inflammatory agents. Drug Des Devel Ther. 2018 May 24;12:1431-1443. doi: 10.2147/DDDT.S154169. eCollection 2018. [PubMed:29872266 ]
Hawas UW, Gamal-Eldeen AM, El-Desouky SK, Kim YK, Huefner A, Saf R: Induction of caspase-8 and death receptors by a new dammarane skeleton from the dried fruits of Forsythia koreana. Z Naturforsch C J Biosci. 2013 Jan-Feb;68(1-2):29-38. [PubMed:23659170 ]
Tang T, Zuo L, Na Z, Xu Y: [Chemical constituents from stems of Dysoxylum laxiracemosum]. Zhongguo Zhong Yao Za Zhi. 2012 May;37(9):1237-40. [PubMed:22803367 ]

Showing NP-Card for Cabralealactone (NP0076286)

MOL for NP0076286 (Cabralealactone)

3D MOL for NP0076286 (Cabralealactone)

3D SDF for NP0076286 (Cabralealactone)

3D-SDF for NP0076286 (Cabralealactone)

PDB for NP0076286 (Cabralealactone)

3D PDB for NP0076286 (Cabralealactone)

SMILES for NP0076286 (Cabralealactone)

INCHI for NP0076286 (Cabralealactone)

Structure for NP0076286 (Cabralealactone)

3D Structure for NP0076286 (Cabralealactone)