NP-MRD: Showing NP-Card for (1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol (NP0255461)

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Record Information

Version

2.0

Created at

2022-09-07 19:58:28 UTC

Updated at

2022-09-07 19:58:28 UTC

NP-MRD ID

NP0255461

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol

Description

Alismol 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. (1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol is found in Alisma plantago-aquatica, Marchantia quadrata and Melampodium divaricatum. (1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol was first documented in 2018 (PMID: 29182515). Based on a literature review a small amount of articles have been published on Alismol (PMID: 31872660) (PMID: 31359656) (PMID: 31275407).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072221582D          

 16 17  0  0  1  0            999 V2000
    3.1690    1.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713   -1.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871   -1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699   -2.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3157   -1.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860   -1.6817    0.0000 O   0  0  0  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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  2  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0255461

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C[C@@H]2[C@H](CC[C@@]2(C)O)C(=C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-10(2)12-6-5-11(3)13-7-8-15(4,16)14(13)9-12/h9-10,13-14,16H,3,5-8H2,1-2,4H3/t13-,14-,15-/m1/s1

> <INCHI_KEY>
BUPJOLXWQXEJSQ-RBSFLKMASA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.356

> <EXACT_MASS>
220.182715393

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.00138817165074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3aS,8aR)-1-methyl-4-methylidene-7-(propan-2-yl)-1,2,3,3a,4,5,6,8a-octahydroazulen-1-ol

> <JCHEM_LOGP>
3.191074143

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.622463696520693

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7769343791418492

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
69.208

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3aS,8aR)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       5.916   2.848   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.720  -2.975   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.243  -2.746   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.157  -4.409   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.456  -2.672   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.894  -3.139   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O

Average Mass

220.3560 Da

Monoisotopic Mass

220.18272 Da

IUPAC Name

(1R,3aS,8aR)-1-methyl-4-methylidene-7-(propan-2-yl)-1,2,3,3a,4,5,6,8a-octahydroazulen-1-ol

Traditional Name

(1R,3aS,8aR)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol

CAS Registry Number

Not Available

SMILES

CC(C)C1=C[C@@H]2[C@H](CC[C@@]2(C)O)C(=C)CC1

InChI Identifier

InChI=1S/C15H24O/c1-10(2)12-6-5-11(3)13-7-8-15(4,16)14(13)9-12/h9-10,13-14,16H,3,5-8H2,1-2,4H3/t13-,14-,15-/m1/s1

InChI Key

BUPJOLXWQXEJSQ-RBSFLKMASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alisma plantago-aquatica	LOTUS Database	35616633
Marchantia quadrata	LOTUS Database	35616633
Melampodium divaricatum	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
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	3.19	ChemAxon
pKa (Strongest Acidic)	19.62	ChemAxon
pKa (Strongest Basic)	-0.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.21 m³·mol⁻¹	ChemAxon
Polarizability	27 Å³	ChemAxon
Number of Rings	2	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

C00020395

Chemspider ID

10470646

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15934381

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

You HM, Zhang JR, Zhao ZH, Wang W, Zhang LZ, Jiang YT, Wang Y, Huang XZ, Jiang ZY: [A new guaiane-type sesquiterpenoid from Croton yunnanensis]. Zhongguo Zhong Yao Za Zhi. 2019 Nov;44(21):4648-4652. doi: 10.19540/j.cnki.cjcmm.20190809.201. [PubMed:31872660 ]
Tai YN, Weng YH, Zhang SP, Xu W, Li XY, Lin QQ, Chu KD, Wu SS: [Determination of seven ingredients of different grades Alismatis Rhizoma by QAMS method]. Zhongguo Zhong Yao Za Zhi. 2019 Jun;44(11):2292-2307. doi: 10.19540/j.cnki.cjcmm.20190321.205. [PubMed:31359656 ]
Abou El-Kassem LT, Hawas UW, El-Desouky SK, Al-Farawati R: Sesquiterpenes from the Saudi Red Sea: Litophyton arboreum with their cytotoxic and antimicrobial activities. Z Naturforsch C J Biosci. 2018 Jan 26;73(1-2):9-14. doi: 10.1515/znc-2017-0037. [PubMed:29182515 ]
Choi E, Jang E, Lee JH: Pharmacological Activities of Alisma orientale against Nonalcoholic Fatty Liver Disease and Metabolic Syndrome: Literature Review. Evid Based Complement Alternat Med. 2019 Jun 3;2019:2943162. doi: 10.1155/2019/2943162. eCollection 2019. [PubMed:31275407 ]
LOTUS database [Link]

Showing NP-Card for (1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol (NP0255461)

MOL for NP0255461 ((1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol)

3D MOL for NP0255461 ((1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol)

3D SDF for NP0255461 ((1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol)

3D-SDF for NP0255461 ((1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol)

PDB for NP0255461 ((1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol)

3D PDB for NP0255461 ((1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol)

SMILES for NP0255461 ((1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol)

INCHI for NP0255461 ((1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol)

Structure for NP0255461 ((1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol)

3D Structure for NP0255461 ((1r,3as,8ar)-7-isopropyl-1-methyl-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-ol)