NP-MRD: Showing NP-Card for (1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one (NP0217111)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 17:20:36 UTC

Updated at

2022-09-05 17:20:36 UTC

NP-MRD ID

NP0217111

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one

Description

Isozedoarondiol belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. (1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one is found in Curcuma aeruginosa, Curcuma aromatica, Curcuma heyneana, Curcuma longa and Curcuma phaeocaulis. (1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one was first documented in 2007 (PMID: 18229613). Based on a literature review a small amount of articles have been published on Isozedoarondiol (PMID: 31726856) (PMID: 23389255) (PMID: 18663560) (PMID: 18098168).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052219202D          

 18 19  0  0  1  0            999 V2000
    3.3158    0.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1986   -0.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    0.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    0.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363    1.1136    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5363    1.9386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2483    2.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333    1.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483    0.8586    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8556    0.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853    0.0499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    2.4530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5363    2.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392    3.1963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    2.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436    1.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686    1.5261    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  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0217111

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C1C[C@H]2[C@@H](CC[C@]2(C)O)[C@](C)(O)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O3/c1-9(2)10-7-12-11(5-6-14(12,3)17)15(4,18)8-13(10)16/h11-12,17-18H,5-8H2,1-4H3/t11-,12+,14+,15-/m1/s1

> <INCHI_KEY>
TXIKNNOOLCGADE-PAPYEOQZSA-N

> <FORMULA>
C15H24O3

> <MOLECULAR_WEIGHT>
252.354

> <EXACT_MASS>
252.172544633

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.15094684519414

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3aR,4R,8aS)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-decahydroazulen-6-one

> <JCHEM_LOGP>
1.6684790029999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.986591548859057

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.357022737543517

> <JCHEM_PKA_STRONGEST_BASIC>
-2.901566956677086

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
71.38519999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3aR,4R,8aS)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       6.189   0.487   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.667   0.257   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.104  -1.176   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.706   1.461   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.205   1.119   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.001   2.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.001   3.619   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.464   4.095   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.369   2.849   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.464   1.603   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.597   0.560   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.159   0.093   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.205   4.579   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.001   5.539   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.873   5.966   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.706   4.236   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.375   2.849   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.915   2.849   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11   12                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16    4   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
Zedoarondiol	MeSH

Chemical Formula

C₁₅H₂₄O₃

Average Mass

252.3540 Da

Monoisotopic Mass

252.17254 Da

IUPAC Name

(1S,3aR,4R,8aS)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-decahydroazulen-6-one

Traditional Name

(1S,3aR,4R,8aS)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one

CAS Registry Number

Not Available

SMILES

CC(C)=C1C[C@H]2[C@@H](CC[C@]2(C)O)[C@](C)(O)CC1=O

InChI Identifier

InChI=1S/C15H24O3/c1-9(2)10-7-12-11(5-6-14(12,3)17)15(4,18)8-13(10)16/h11-12,17-18H,5-8H2,1-4H3/t11-,12+,14+,15-/m1/s1

InChI Key

TXIKNNOOLCGADE-PAPYEOQZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Curcuma aeruginosa	LOTUS Database	35616633
Curcuma aromatica	LOTUS Database	35616633
Curcuma heyneana	LOTUS Database	35616633
Curcuma longa	LOTUS Database	35616633
Curcuma phaeocaulis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Guaianes

Alternative Parents

Substituents

Guaiane sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.67	ChemAxon
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.39 m³·mol⁻¹	ChemAxon
Polarizability	28.15 Å³	ChemAxon
Number of Rings	2	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

Not Available

KNApSAcK ID

C00030554

Chemspider ID

10251991

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14632998

PDB ID

Not Available

ChEBI ID

138763

Good Scents ID

Not Available

References

General References

Al-Amin M, Eltayeb NM, Khairuddean M, Salhimi SM: Bioactive chemical constituents from Curcuma caesia Roxb. rhizomes and inhibitory effect of curcuzederone on the migration of triple-negative breast cancer cell line MDA-MB-231. Nat Prod Res. 2021 Sep;35(18):3166-3170. doi: 10.1080/14786419.2019.1690489. Epub 2019 Nov 15. [PubMed:31726856 ]
Zhu JJ, An YW, Hu G, Yin GP, Zhang QW, Wang ZM: Simultaneous determination of multiple sesquiterpenes in Curcuma wenyujin herbal medicines and related products with one single reference standard. Molecules. 2013 Feb 6;18(2):2110-21. doi: 10.3390/molecules18022110. [PubMed:23389255 ]
Qu Y, Xu F, Nakamura S, Matsuda H, Pongpiriyadacha Y, Wu L, Yoshikawa M: Sesquiterpenes from Curcuma comosa. J Nat Med. 2009 Jan;63(1):102-4. doi: 10.1007/s11418-008-0282-8. Epub 2008 Jul 29. [PubMed:18663560 ]
Wang SS, Zhang JM, Guo XH, Song QL, Zhao WJ: A new eudesmane sesquiterpene lactone from Curcuma wenyujin. Yao Xue Xue Bao. 2007 Oct;42(10):1062-5. [PubMed:18229613 ]
Jia N, Xiao Chi M, Xiu Lan X, Hong Wei J, Dean G: Structural determination of two new sesquiterpenes biotransformed from germacrone by Mucor alternata. Magn Reson Chem. 2008 Feb;46(2):178-81. doi: 10.1002/mrc.2148. [PubMed:18098168 ]
LOTUS database [Link]

Showing NP-Card for (1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one (NP0217111)

MOL for NP0217111 ((1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one)

3D MOL for NP0217111 ((1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one)

3D SDF for NP0217111 ((1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one)

3D-SDF for NP0217111 ((1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one)

PDB for NP0217111 ((1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one)

3D PDB for NP0217111 ((1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one)

SMILES for NP0217111 ((1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one)

INCHI for NP0217111 ((1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one)

Structure for NP0217111 ((1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one)

3D Structure for NP0217111 ((1s,3ar,4r,8as)-1,4-dihydroxy-1,4-dimethyl-7-(propan-2-ylidene)-hexahydroazulen-6-one)