NP-MRD: Showing NP-Card for Arborescin (NP0063728)

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Record Information

Version

2.0

Created at

2022-04-28 08:05:06 UTC

Updated at

2022-04-28 08:05:06 UTC

NP-MRD ID

NP0063728

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arborescin

Description

Arborescin belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Arborescin is found in Artemisia adamsii, Artemisia arborescens , Artemisia argentea, Artemisia austriaca and Artemisia gorgonum. Arborescin was first documented in 1995 (PMID: 7617767). Based on a literature review very few articles have been published on arborescin (PMID: 21997763).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
   -1.3503    3.2128   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6448    1.8059    0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8807    1.3801    0.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9011   -0.0549    0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5344   -0.5097    0.2570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4971   -1.1932   -0.9797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1488   -1.7988    0.2871 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1802   -2.8833    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2540   -2.2679    0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2028   -1.6141   -0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342   -0.2131   -0.0917 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7643    0.3440   -0.7358 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8927    0.5549    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3620    1.6640   -1.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0900    2.3768   -2.0031 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0890    1.9072   -0.7667 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4330    0.6841   -0.6523 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6911    0.6819    0.3530 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4789    3.3653   -1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3490    3.5305    0.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0776    3.8897    0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7963    1.9716    0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6732   -0.6254    0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0055   -0.1457    1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0292   -2.3954    1.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5528   -3.3659   -0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7255   -3.5836    1.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6916   -2.1691    1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2957   -3.3740    0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847   -1.5248   -1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1170   -2.2025   -0.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5478   -0.1473    1.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1525   -0.3295   -1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4277   -0.4037    0.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5727    1.3497   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    0.9293    1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412    0.3005   -1.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2277    0.8538    1.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  1
  7  6  1  0
  5  6  1  6
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 18  1  0
 18 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 14 12  1  0
 17 11  1  0
  5  7  1  0
 18  5  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 12 33  1  6
 11 32  1  1
 10 30  1  0
 10 31  1  0
  9 28  1  0
  9 29  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  4 23  1  0
  4 24  1  0
  3 22  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 18 38  1  1
 17 37  1  6
M  END


  Mrv1652304282210052D          

 18 21  0  0  1  0            999 V2000
   -0.0435   -1.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7635   -1.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498   -0.2624    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0961    0.0732    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4560   -0.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114    0.8716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3835    1.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2081    1.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7415    0.9270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5820    0.1175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3026   -0.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9074    0.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168    0.1173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5606    1.0254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9624    1.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6992    0.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7327    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3765   -1.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
  6 16  1  0  0  0  0
  4 16  1  1  0  0  0
  6 17  1  6  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063728

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H]2CC[C@]3(C)O[C@@]33CC=C(C)[C@@H]3[C@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-4-7-15-11(8)12-10(9(2)13(16)17-12)5-6-14(15,3)18-15/h4,9-12H,5-7H2,1-3H3/t9-,10-,11+,12-,14-,15+/m0/s1

> <INCHI_KEY>
CBRKCJOSZHRKFH-UVGOUCATSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.549244103992567

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,6S,7S,10S,11R)-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradec-12-en-8-one

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
2.0300196930000003

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.254953502529634

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
66.9873

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,6S,7S,10S,11R)-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradec-12-en-8-one

> <JCHEM_VEBER_RULE>
1

$$$$

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      -0.081  -2.342   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.425  -2.021   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.586  -0.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.179   0.137   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.851  -1.008   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.208   1.627   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.716   2.859   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.255   2.905   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.251   1.730   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.953   0.219   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.298  -0.531   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.427   0.517   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.938   0.219   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.780   1.914   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.530   3.259   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.305   0.546   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.368   2.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.570  -3.052   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6   16                                             
CONECT    5    4    1                                                       
CONECT    6    4    7   16   17                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    9   15                                                  
CONECT   15   14                                                            
CONECT   16    6    4                                                       
CONECT   17    6                                                            
CONECT   18    2                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Value	Source
1,10-Epoxy-6beta-hydroxy-1beta,5beta,7alpha-guiai-3-en-12-Oic acid gamma-lactone	ChEBI
1,10-Epoxy-6b-hydroxy-1b,5b,7a-guiai-3-en-12-Oate g-lactone	Generator
1,10-Epoxy-6b-hydroxy-1b,5b,7a-guiai-3-en-12-Oic acid g-lactone	Generator
1,10-Epoxy-6beta-hydroxy-1beta,5beta,7alpha-guiai-3-en-12-Oate gamma-lactone	Generator
1,10-Epoxy-6β-hydroxy-1β,5β,7α-guiai-3-en-12-Oate γ-lactone	Generator
1,10-Epoxy-6β-hydroxy-1β,5β,7α-guiai-3-en-12-Oic acid γ-lactone	Generator

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(1R,3S,6S,7S,10S,11R)-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradec-12-en-8-one

Traditional Name

(1R,3S,6S,7S,10S,11R)-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradec-12-en-8-one

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H]2CC[C@]3(C)O[C@@]33CC=C(C)[C@@H]3[C@H]2OC1=O

InChI Identifier

InChI=1S/C15H20O3/c1-8-4-7-15-11(8)12-10(9(2)13(16)17-12)5-6-14(15,3)18-15/h4,9-12H,5-7H2,1-3H3/t9-,10-,11+,12-,14-,15+/m0/s1

InChI Key

CBRKCJOSZHRKFH-UVGOUCATSA-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
Artemisia adamsii	LOTUS Database	35616633
Artemisia arborescens	Plant	KNApSAcK
Artemisia argentea	LOTUS Database	35616633
Artemisia austriaca	LOTUS Database	35616633
Artemisia gorgonum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

organic heterotetracyclic compound (CHEBI:73226 )
epoxide (CHEBI:73226 )
gamma-lactone (CHEBI:73226 )
sesquiterpene lactone (CHEBI:73226 )

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	3.18	ALOGPS
logP	2.03	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-4.3	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	66.99 m³·mol⁻¹	ChemAxon
Polarizability	27.55 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

C00020611

Chemspider ID

9981679

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11807014

PDB ID

Not Available

ChEBI ID

73226

Good Scents ID

Not Available

References

General References

Csuk R, Heinold A, Siewert B, Schwarz S, Barthel A, Kluge R, Strohl D: Synthesis and biological evaluation of antitumor-active arglabin derivatives. Arch Pharm (Weinheim). 2012 Mar;345(3):215-22. doi: 10.1002/ardp.201100065. Epub 2011 Oct 14. [PubMed:21997763 ]
Abu Zarga M, Qauasmeh R, Sabri S, Munsoor M, Abdalla S: Chemical constituents of Artemisia arborescens and the effect of the aqueous extract on rat isolated smooth muscle. Planta Med. 1995 Jun;61(3):242-5. doi: 10.1055/s-2006-958064. [PubMed:7617767 ]

Showing NP-Card for Arborescin (NP0063728)

MOL for NP0063728 (Arborescin)

3D MOL for NP0063728 (Arborescin)

3D SDF for NP0063728 (Arborescin)

3D-SDF for NP0063728 (Arborescin)

PDB for NP0063728 (Arborescin)

3D PDB for NP0063728 (Arborescin)

SMILES for NP0063728 (Arborescin)

INCHI for NP0063728 (Arborescin)

Structure for NP0063728 (Arborescin)

3D Structure for NP0063728 (Arborescin)