NP-MRD: Showing NP-Card for Proazulene (NP0046934)

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Record Information

Version

2.0

Created at

2022-03-17 20:31:55 UTC

Updated at

2022-03-17 20:31:55 UTC

NP-MRD ID

NP0046934

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Proazulene

Description

Proazulene is found in Achillea collina , Achillea collina J.Becker ex Reichenb , Artemisia arborescens , Artemisia vallesiaca and Matricaria chamomilla.

Structure

MOL SDF PDB SMILES InChI

  Mrv1533007131513472D          

 27 29  0  0  1  0            999 V2000
    3.6754   -0.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    0.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767   -1.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4218    2.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871   -0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    1.4145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0217   -1.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.3203    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3602    1.1246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6996    1.7696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8746    1.7696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6248    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    2.4581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7897   -1.3113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4555    3.2261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -0.1941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    2.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802    0.5947    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1888    0.8347    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407    1.9199    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3086    2.4961    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325    1.0263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  6  0  0  0
 10  3  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17  4  1  1  0  0  0
 17  6  1  0  0  0  0
 17 14  1  0  0  0  0
 18 10  2  0  0  0  0
 19 16  2  0  0  0  0
 17 20  1  6  0  0  0
 21 10  1  0  0  0  0
 12 21  1  1  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
  9 23  1  1  0  0  0
 12 24  1  1  0  0  0
 13 25  1  6  0  0  0
 14 26  1  6  0  0  0
 15 27  1  1  0  0  0
M  END

  Mrv1533007131513472D          

 27 29  0  0  1  0            999 V2000
    3.6754   -0.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    0.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767   -1.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4218    2.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871   -0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    1.4145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0217   -1.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.3203    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3602    1.1246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6996    1.7696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8746    1.7696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6248    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    2.4581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7897   -1.3113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4555    3.2261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -0.1941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    2.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802    0.5947    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1888    0.8347    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407    1.9199    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3086    2.4961    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2325    1.0263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  6  0  0  0
 10  3  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17  4  1  1  0  0  0
 17  6  1  0  0  0  0
 17 14  1  0  0  0  0
 18 10  2  0  0  0  0
 19 16  2  0  0  0  0
 17 20  1  6  0  0  0
 21 10  1  0  0  0  0
 12 21  1  1  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
  9 23  1  1  0  0  0
 12 24  1  1  0  0  0
 13 25  1  6  0  0  0
 14 26  1  6  0  0  0
 15 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0046934

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(C)C(=O)O[C@]2([H])[C@]3([H])C(C=C[C@@]3(C)O)=C(C)C[C@]([H])(OC(C)=O)[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-8-7-12(21-10(3)18)13-9(2)16(19)22-15(13)14-11(8)5-6-17(14,4)20/h5-6,9,12-15,20H,7H2,1-4H3/t9-,12-,13+,14-,15-,17+/m0/s1

> <INCHI_KEY>
SYTRJRUSWMMZLV-VQGWEXQJSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.358

> <EXACT_MASS>
306.146723808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.31262489902722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aR,4S,9R,9aS,9bS)-9-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
0.7180000146666667

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.235042785360864

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1333922856831586

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
80.54149999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
matricin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       6.861  -0.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.188   1.792   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.703  -2.845   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.521   5.298   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.441   2.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.372   4.179   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.269  -0.070   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.657   0.598   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.097   2.640   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.907  -1.885   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.999   2.099   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.882   0.598   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.539   2.099   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.039   3.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.499   3.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.166   4.179   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.888   4.589   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.341  -2.448   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.038   5.139   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.450   6.022   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.678  -0.362   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.651   4.589   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       1.270   1.110   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.086   1.558   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.129   3.584   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.309   4.659   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.167   1.916   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   17                                                            
CONECT    5    6   11                                                       
CONECT    6    5   17                                                       
CONECT    7    8   12                                                       
CONECT    8    1    7   11                                                  
CONECT    9    2   13   16   23                                             
CONECT   10    3   18   21                                                  
CONECT   11    5    8   14                                                  
CONECT   12    7   13   21   24                                             
CONECT   13    9   12   15   25                                             
CONECT   14   11   15   17   26                                             
CONECT   15   13   14   22   27                                             
CONECT   16    9   19   22                                                  
CONECT   17    4    6   14   20                                             
CONECT   18   10                                                            
CONECT   19   16                                                            
CONECT   20   17                                                            
CONECT   21   10   12                                                       
CONECT   22   15   16                                                       
CONECT   23    9                                                            
CONECT   24   12                                                            
CONECT   25   13                                                            
CONECT   26   14                                                            
CONECT   27   15                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
Matricine	MeSH

Chemical Formula

C₁₇H₂₂O₅

Average Mass

306.3580 Da

Monoisotopic Mass

306.14672 Da

IUPAC Name

(3S,3aR,4S,9R,9aS,9bS)-9-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

Traditional Name

matricin

CAS Registry Number

29041-35-8

SMILES

[H][C@@]1(C)C(=O)O[C@]2([H])[C@]3([H])C(C=C[C@@]3(C)O)=C(C)C[C@]([H])(OC(C)=O)[C@@]12[H]

InChI Identifier

InChI=1S/C17H22O5/c1-8-7-12(21-10(3)18)13-9(2)16(19)22-15(13)14-11(8)5-6-17(14,4)20/h5-6,9,12-15,20H,7H2,1-4H3/t9-,12-,13+,14-,15-,17+/m0/s1

InChI Key

SYTRJRUSWMMZLV-VQGWEXQJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea collina	Plant	KNApSAcK
Achillea collina J.Becker ex Reichenb	Plant	KNApSAcK
Artemisia arborescens	Plant	KNApSAcK
Artemisia vallesiaca	LOTUS Database	35616633
Matricaria chamomilla	LOTUS Database	35616633
Pimpinella anisum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Dicarboxylic acid or derivatives
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Oxacycle
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

sesquiterpene lactone (CHEBI:6699 )
Guaiane sesquiterpenoids (C09499 )
Sesquiterpenoids (C15) (C09499 )
Guaiane sesquiterpenoids (LMPR0103410003 )

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	1.84	ALOGPS
logP	0.72	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.24	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.54 m³·mol⁻¹	ChemAxon
Polarizability	32.31 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

FDB006586

KNApSAcK ID

C00003321

Chemspider ID

Not Available

KEGG Compound ID

C09499

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Matricin

METLIN ID

Not Available

PubChem Compound

92265

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Proazulene (NP0046934)

MOL for NP0046934 (Proazulene)

3D MOL for NP0046934 (Proazulene)

3D SDF for NP0046934 (Proazulene)

3D-SDF for NP0046934 (Proazulene)

PDB for NP0046934 (Proazulene)

3D PDB for NP0046934 (Proazulene)

SMILES for NP0046934 (Proazulene)

INCHI for NP0046934 (Proazulene)

Structure for NP0046934 (Proazulene)

3D Structure for NP0046934 (Proazulene)