NP-MRD: Showing NP-Card for Austricin (NP0048519)

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Record Information

Version

2.0

Created at

2022-03-17 20:57:44 UTC

Updated at

2022-03-17 20:57:44 UTC

NP-MRD ID

NP0048519

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Austricin

Description

Austricin is found in Achillea abrotanoides, Achillea alpina, Achillea collina , Achillea collina J.Becker ex Reichenb , Achillea lanulosa, Achillea ligustica, Achillea millefolium, Achillea santolina, Achillea sibirica, Achillea vermicularis, Artemisia austriaca, Artemisia cana, Artemisia caucasica, Artemisia deserti, Artemisia frigide, Artemisia incana, Artemisia juncea, Artemisia klotzchiana, Artemisia leucodes, Artemisia myriantha, Artemisia splendens, Artemisia tilesii, Artemisia xerophytica, Cichorium intybus, Dendroseris neriifolia, Dendroseris neriifolia Hook.& Arn., Lactuca tatarica, Notoseris gracilipes C. Shih, Notoseris henryi (Dunn) C. Shih, Notoseris psilolepis C. Shih, Notoseris rhombiformis C. Shih, Notoseris triflora (Hemsl.) C .Shih, Picris koreana (Kitam.) Vorosch. , Reichardia crystallina (Sch.Bip.ex Webb & Berthault) Bramwell, Reichardia tingitana (L.) Roth , Tanacetum macrophyllum, Tanacetum microphyllum, Taraxacum alpinum, Taraxacum alpinum (Hoppe) Hegetschw., Taraxacum bessarabicum (Hornem.) Hand-Mazz., Taraxacum hondoense Nakai ex Koidz., Taraxacum obovatum, Taraxacum obovatum DC. , Taraxacum platycarpum and Taraxacum platycarpum Dahist. .

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241217252D          

 19 21  0  0  0  0            999 V2000
   -1.3201   -1.7328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425   -1.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0822   -1.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7425   -1.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023   -1.6506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6596    1.7328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9077    0.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324    0.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324   -0.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3929   -0.5770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9077   -0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124    0.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4124    0.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9077   -0.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6502   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3929   -0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8247    0.9895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5673    0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2277    1.4026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 11  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 14  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048519

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(OC1=O)C1C(C)=CC(=O)C1=C(C)CC2O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-6-4-10(17)13-8(3)15(18)19-14(13)12-7(2)5-9(16)11(6)12/h5,8,10,12-14,17H,4H2,1-3H3

> <INCHI_KEY>
YMUOZXZDDBRJEP-UHFFFAOYSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.301

> <EXACT_MASS>
262.120509064

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.67706470411067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3,6,9-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
1.1213753326666667

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.626424201981763

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.578780422018742

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9001623975370725

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
70.28699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3,6,9-trimethyl-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.464  -3.235   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.386  -2.157   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.153  -2.773   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.386  -2.002   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.618  -3.081   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.231   3.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.694   1.694   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.234   1.232   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.234  -0.307   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.467  -1.077   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.694  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.770   0.461   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.770   0.616   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.694  -0.616   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -0.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.467  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.539   1.847   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.926   1.539   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.158   2.618   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    2    9   12                                                  
CONECT   12    7   11   13                                                  
CONECT   13   12   14   17                                                  
CONECT   14    4   13   15                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15                                                            
CONECT   17   13   18                                                       
CONECT   18   15   17   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
Desacetylmatricarin	MeSH
Hydroxyachillin	MeSH

Chemical Formula

C₁₅H₁₈O₄

Average Mass

262.3010 Da

Monoisotopic Mass

262.12051 Da

IUPAC Name

4-hydroxy-3,6,9-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

Traditional Name

4-hydroxy-3,6,9-trimethyl-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

CAS Registry Number

10180-88-8

SMILES

CC1C2C(OC1=O)C1C(C)=CC(=O)C1=C(C)CC2O

InChI Identifier

InChI=1S/C15H18O4/c1-6-4-10(17)13-8(3)15(18)19-14(13)12-7(2)5-9(16)11(6)12/h5,8,10,12-14,17H,4H2,1-3H3

InChI Key

YMUOZXZDDBRJEP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea abrotanoides	LOTUS Database	35616633
Achillea alpina	LOTUS Database	35616633
Achillea collina	Plant	KNApSAcK
Achillea collina J.Becker ex Reichenb	Plant	KNApSAcK
Achillea lanulosa	Plant	KNApSAcK
Achillea ligustica	LOTUS Database	35616633
Achillea millefolium	LOTUS Database	35616633
Achillea santolina	LOTUS Database	35616633
Achillea sibirica	LOTUS Database	35616633
Achillea vermicularis	LOTUS Database	35616633
Artemisia austriaca	Plant	KNApSAcK
Artemisia cana	LOTUS Database	35616633
Artemisia caucasica	Plant	KNApSAcK
Artemisia deserti	LOTUS Database	35616633
Artemisia frigide	Plant	KNApSAcK
Artemisia incana	LOTUS Database	35616633
Artemisia juncea	LOTUS Database	35616633
Artemisia klotzchiana	LOTUS Database	35616633
Artemisia leucodes	Plant	KNApSAcK
Artemisia myriantha	Plant	KNApSAcK
Artemisia splendens	LOTUS Database	35616633
Artemisia tilesii	Plant	KNApSAcK
Artemisia xerophytica	LOTUS Database	35616633
Cichorium intybus	LOTUS Database	35616633
Dendroseris neriifolia	Plant	KNApSAcK
Dendroseris neriifolia Hook.& Arn.	Plant	KNApSAcK
Lactuca tatarica	LOTUS Database	35616633
Laurus nobilis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Matricaria recutita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Notoseris gracilipes C. Shih	Plant	KNApSAcK
Notoseris henryi (Dunn) C. Shih	Plant	KNApSAcK
Notoseris psilolepis C. Shih	Plant	KNApSAcK
Notoseris rhombiformis C. Shih	Plant	KNApSAcK
Notoseris triflora (Hemsl.) C .Shih	Plant	KNApSAcK
Picris koreana (Kitam.) Vorosch.	Plant	KNApSAcK
Reichardia crystallina (Sch.Bip.ex Webb & Berthault) Bramwell	Plant	KNApSAcK
Reichardia tingitana (L.) Roth	Plant	KNApSAcK
Tanacetum macrophyllum	LOTUS Database	35616633
Tanacetum microphyllum	LOTUS Database	35616633
Taraxacum alpinum	LOTUS Database	35616633
Taraxacum alpinum (Hoppe) Hegetschw.	Plant	KNApSAcK
Taraxacum bessarabicum (Hornem.) Hand-Mazz.	Plant	KNApSAcK
Taraxacum hondoense Nakai ex Koidz.	Plant	KNApSAcK
Taraxacum obovatum	LOTUS Database	35616633
Taraxacum obovatum DC.	Plant	KNApSAcK
Taraxacum platycarpum	LOTUS Database	35616633
Taraxacum platycarpum Dahist.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.02	ALOGPS
logP	1.12	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.29 m³·mol⁻¹	ChemAxon
Polarizability	27.68 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

FDB015365

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

99114

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Austricin (NP0048519)

MOL for NP0048519 (Austricin)

3D MOL for NP0048519 (Austricin)

3D SDF for NP0048519 (Austricin)

3D-SDF for NP0048519 (Austricin)

PDB for NP0048519 (Austricin)

3D PDB for NP0048519 (Austricin)

SMILES for NP0048519 (Austricin)

INCHI for NP0048519 (Austricin)

Structure for NP0048519 (Austricin)

3D Structure for NP0048519 (Austricin)