NP-MRD: Showing NP-Card for (1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one (NP0302946)

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Record Information

Version

2.0

Created at

2022-09-10 16:51:08 UTC

Updated at

2022-09-10 16:51:09 UTC

NP-MRD ID

NP0302946

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one

Description

Ludartin belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. (1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one is found in Artemisia douglasiana, Artemisia mesatlantica, Artemisia sieversiana and Inulanthera calva. (1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one was first documented in 2017 (PMID: 28732812). Based on a literature review a small amount of articles have been published on Ludartin (PMID: 35634434) (PMID: 33704261) (PMID: 32036379) (PMID: 30008466).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309102218512D          

 18 21  0  0  1  0            999 V2000
    6.5532   -1.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7593   -1.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4741   -0.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9328    0.3539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6497   -0.3638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4254   -1.1578    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1111   -1.6164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1801   -2.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5803   -3.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7634   -2.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3048   -3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3446   -2.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5207   -2.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061   -1.3399    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2618   -0.5161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9974   -0.8896    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4457   -0.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6392   -1.4079    0.0000 C   0  0  2  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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 12  1  6  0  0  0
  6 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302946

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C[C@H]3O[C@@]3(C)[C@@H]2[C@H]2OC(=O)C(=C)[C@@H]2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-7-4-5-9-8(2)14(16)17-13(9)12-10(7)6-11-15(12,3)18-11/h9,11-13H,2,4-6H2,1,3H3/t9-,11+,12-,13-,15+/m0/s1

> <INCHI_KEY>
QXJYIGSXUBOSID-JZEMPJKHSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.306

> <EXACT_MASS>
246.12559444

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.71009385700474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,6S,12R,14S)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradec-9-en-4-one

> <JCHEM_LOGP>
2.0565052706666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.230811460816294

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
66.5115

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6S,12R,14S)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradec-9-en-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      12.233  -2.483   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.751  -2.065   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.218  -0.619   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.075   0.661   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.679  -0.679   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.261  -2.161   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.541  -3.017   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.669  -4.552   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.550  -5.609   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.025  -5.393   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.169  -6.673   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.243  -4.067   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.705  -3.988   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.305  -2.501   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.222  -0.963   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.595  -1.661   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.432  -0.368   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.793  -2.628   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   16                                                       
CONECT   16   15   14   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   12    6                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₃

Average Mass

246.3060 Da

Monoisotopic Mass

246.12559 Da

IUPAC Name

(1S,2S,6S,12R,14S)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradec-9-en-4-one

Traditional Name

(1S,2S,6S,12R,14S)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradec-9-en-4-one

CAS Registry Number

Not Available

SMILES

CC1=C2C[C@H]3O[C@@]3(C)[C@@H]2[C@H]2OC(=O)C(=C)[C@@H]2CC1

InChI Identifier

InChI=1S/C15H18O3/c1-7-4-5-9-8(2)14(16)17-13(9)12-10(7)6-11-15(12,3)18-11/h9,11-13H,2,4-6H2,1,3H3/t9-,11+,12-,13-,15+/m0/s1

InChI Key

QXJYIGSXUBOSID-JZEMPJKHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia douglasiana	LOTUS Database	35616633
Artemisia mesatlantica	LOTUS Database	35616633
Artemisia sieversiana	LOTUS Database	35616633
Inulanthera calva	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Sesquiterpenoid
Gamma butyrolactone
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen 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	2.06	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.51 m³·mol⁻¹	ChemAxon
Polarizability	26.71 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00020570

Chemspider ID

19992327

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14355826

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sun JJ, Wang JP, Li TZ, Ma YB, Xue D, Chen JJ: Design and synthesis of ludartin derivatives as potential anticancer agents against hepatocellular carcinoma. Med Chem Res. 2022;31(7):1224-1239. doi: 10.1007/s00044-022-02890-2. Epub 2022 May 24. [PubMed:35634434 ]
Zhang SL, Li BL, Li W, Lu M, Ni LY, Ma HL, Meng QG: Retracted: The Effects of Ludartin on Cell Proliferation, Cell Migration, Cell Cycle Arrest and Apoptosis Are Associated with Upregulation of p21WAF1 in Saos-2 Osteosarcoma Cells In Vitro. Med Sci Monit. 2021 Mar 11;27:e931590. doi: 10.12659/MSM.931590. [PubMed:33704261 ]
Wang L, Wang L, Wei S, Wang X, Shen D: The Effects of (11R)-13-(6-Nitroindazole)-11,13-Dihydroludartin on Human Prostate Carcinoma Cells and Mouse Tumor Xenografts. Med Sci Monit. 2020 Feb 9;26:e920389. doi: 10.12659/MSM.920389. [PubMed:32036379 ]
Zhang SL, Li BL, Li W, Lu M, Ni LY, Ma HL, Meng QG: The Effects of Ludartin on Cell Proliferation, Cell Migration, Cell Cycle Arrest and Apoptosis Are Associated with Upregulation of p21WAF1 in Saos-2 Osteosarcoma Cells In Vitro. Med Sci Monit. 2018 Jul 16;24:4926-4933. doi: 10.12659/MSM.909193. [PubMed:30008466 ]
Giorgi A, Bassoli A, Borgonovo G, Panseri S, Manzo A, Pentimalli D, Schiano Moriello A, De Petrocellis L: Extracts and compounds active on TRP ion channels from Waldheimia glabra, a ritual medicinal plant from Himalaya. Phytomedicine. 2017 Aug 15;32:80-87. doi: 10.1016/j.phymed.2017.04.012. Epub 2017 May 1. [PubMed:28732812 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one (NP0302946)

MOL for NP0302946 ((1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one)

3D MOL for NP0302946 ((1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one)

3D SDF for NP0302946 ((1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one)

3D-SDF for NP0302946 ((1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one)

PDB for NP0302946 ((1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one)

3D PDB for NP0302946 ((1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one)

SMILES for NP0302946 ((1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one)

INCHI for NP0302946 ((1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one)

Structure for NP0302946 ((1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one)

3D Structure for NP0302946 ((1s,2s,6s,12r,14s)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradec-9-en-4-one)