NP-MRD: Showing NP-Card for Kulactone (NP0080682)

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Record Information

Version

2.0

Created at

2022-04-29 01:40:54 UTC

Updated at

2022-04-29 01:40:54 UTC

NP-MRD ID

NP0080682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kulactone

Description

KULACTONE belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Kulactone is found in Azadirachta indica, Melia azedarach , Melia dubia and Melia volkensii. Kulactone was first documented in 2002 (PMID: 12502333). Based on a literature review a small amount of articles have been published on KULACTONE (PMID: 31979199) (PMID: 34518560) (PMID: 26517430).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203402D          

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  6 31  1  6  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC[C@@H]1[C@@H]2[C@H](C[C@]3(C)C4=CC[C@H]5C(C)(C)C(=O)CC[C@]5(C)[C@H]4CC[C@@]23C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O3/c1-18(2)9-8-10-19-25-22(33-26(19)32)17-30(7)21-11-12-23-27(3,4)24(31)14-15-28(23,5)20(21)13-16-29(25,30)6/h9,11,19-20,22-23,25H,8,10,12-17H2,1-7H3/t19-,20+,22+,23+,25-,28-,29+,30-/m1/s1

> <INCHI_KEY>
ZIVZDNPCRURPNL-QCWHEMHRSA-N

> <FORMULA>
C30H44O3

> <MOLECULAR_WEIGHT>
452.679

> <EXACT_MASS>
452.329045277

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.534070580678716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4S,7R,8S,9S,12R,13R,18R)-2,9,13,17,17-pentamethyl-7-(4-methylpent-3-en-1-yl)-5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-1(20)-ene-6,16-dione

> <ALOGPS_LOGP>
7.12

> <JCHEM_LOGP>
6.605289795999999

> <ALOGPS_LOGS>
-5.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.9117333383228

> <JCHEM_PKA_STRONGEST_BASIC>
-6.935906926390352

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
133.7806

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,7R,8S,9S,12R,13R,18R)-2,9,13,17,17-pentamethyl-7-(4-methylpent-3-en-1-yl)-5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-1(20)-ene-6,16-dione

> <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      10.125   6.192   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.744   4.781   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.274   4.612   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.832   3.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.301   3.710   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.683   5.120   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.595   6.361   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.152   5.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.240   4.049   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.858   2.639   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.389   2.469   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.709   4.219   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.091   5.629   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.003   6.870   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.533   6.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.558   5.477   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.230   3.972   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.559   3.195   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.303   3.820   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.921   5.230   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.426   5.559   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.229   6.254   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.077   7.787   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.328   8.685   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.175  10.217   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.426  11.116   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.274  12.648   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.829  10.481   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.328   6.967   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.177   2.752   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.064   6.531   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.040   2.586   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.716   2.005   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32   33                                             
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8   31                                             
CONECT    7    6    1                                                       
CONECT    8    6    9   15                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5                                                       
CONECT   12    9   13   18   30                                             
CONECT   13   12   14   16   29                                             
CONECT   14   13   15                                                       
CONECT   15   14    8                                                       
CONECT   16   13   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   12                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   16   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   13                                                            
CONECT   30   12                                                            
CONECT   31    6                                                            
CONECT   32    4                                                            
CONECT   33    4                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₃

Average Mass

452.6790 Da

Monoisotopic Mass

452.32905 Da

IUPAC Name

(2S,4S,7R,8S,9S,12R,13R,18R)-2,9,13,17,17-pentamethyl-7-(4-methylpent-3-en-1-yl)-5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-1(20)-ene-6,16-dione

Traditional Name

(2S,4S,7R,8S,9S,12R,13R,18R)-2,9,13,17,17-pentamethyl-7-(4-methylpent-3-en-1-yl)-5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-1(20)-ene-6,16-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@@H]1[C@@H]2[C@H](C[C@]3(C)C4=CC[C@H]5C(C)(C)C(=O)CC[C@]5(C)[C@H]4CC[C@@]23C)OC1=O

InChI Identifier

InChI=1S/C30H44O3/c1-18(2)9-8-10-19-25-22(33-26(19)32)17-30(7)21-11-12-23-27(3,4)24(31)14-15-28(23,5)20(21)13-16-29(25,30)6/h9,11,19-20,22-23,25H,8,10,12-17H2,1-7H3/t19-,20+,22+,23+,25-,28-,29+,30-/m1/s1

InChI Key

ZIVZDNPCRURPNL-QCWHEMHRSA-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
Azadirachta indica	LOTUS Database	35616633
Melia azedarach	Plant	KNApSAcK
Melia dubia	Plant	KNApSAcK
Melia volkensii	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-oxo-delta-7-steroid
3-oxosteroid
Oxosteroid
3-oxo-5-alpha-steroid
Delta-7-steroid
Steroid
Gamma butyrolactone
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	7.12	ALOGPS
logP	6.61	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	19.91	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	3	ChemAxon
Refractivity	133.78 m³·mol⁻¹	ChemAxon
Polarizability	54.53 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

C00010616

Chemspider ID

23340023

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15560423

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pettit GR, Numata A, Iwamoto C, Morito H, Yamada T, Goswami A, Clewlow PJ, Cragg GM, Schmidt JM: Antineoplastic agents. 489. Isolation and structures of meliastatins 1-5 and related euphane triterpenes from the tree Melia dubia. J Nat Prod. 2002 Dec;65(12):1886-91. doi: 10.1021/np020216+. [PubMed:12502333 ]
Jaoko V, Nji Tizi Taning C, Backx S, Mulatya J, Van den Abeele J, Magomere T, Olubayo F, Mangelinckx S, Werbrouck SPO, Smagghe G: The Phytochemical Composition of Melia volkensii and Its Potential for Insect Pest Management. Plants (Basel). 2020 Jan 22;9(2):143. doi: 10.3390/plants9020143. [PubMed:31979199 ]
Dwivedi VD, Singh A, El-Kafraway SA, Alandijany TA, Faizo AA, Bajrai LH, Kamal MA, Azhar EI: Mechanistic insights into the Japanese encephalitis virus RNA dependent RNA polymerase protein inhibition by bioflavonoids from Azadirachta indica. Sci Rep. 2021 Sep 13;11(1):18125. doi: 10.1038/s41598-021-96917-0. [PubMed:34518560 ]
Kamau RW, Juma BF, Baraza LD: Antimicrobial compounds from root, stem bark and seeds of Melia volkensii. Nat Prod Res. 2016 Sep;30(17):1984-7. doi: 10.1080/14786419.2015.1101104. Epub 2015 Oct 30. [PubMed:26517430 ]

Showing NP-Card for Kulactone (NP0080682)

MOL for NP0080682 (Kulactone)

3D MOL for NP0080682 (Kulactone)

3D SDF for NP0080682 (Kulactone)

3D-SDF for NP0080682 (Kulactone)

PDB for NP0080682 (Kulactone)

3D PDB for NP0080682 (Kulactone)

SMILES for NP0080682 (Kulactone)

INCHI for NP0080682 (Kulactone)

Structure for NP0080682 (Kulactone)

3D Structure for NP0080682 (Kulactone)