NP-MRD: Showing NP-Card for (1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate (NP0175581)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 13:05:06 UTC

Updated at

2022-09-03 13:05:06 UTC

NP-MRD ID

NP0175581

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate

Description

Trans-Sabinyl acetate belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate is found in Daucus carota. (1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate was first documented in 2014 (PMID: 25632489). Based on a literature review a small amount of articles have been published on trans-Sabinyl acetate (PMID: 26404704) (PMID: 33673548) (PMID: 29421510) (PMID: 28488391).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    1.2504    0.1079    2.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6004    0.1868    1.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1877    0.3557    0.0422 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5276   -0.0876   -0.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900    0.7801   -0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9364    0.3683   -0.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1165    1.9241   -0.8701 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2780   -0.5500   -0.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708   -0.3679   -0.1721 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2041    0.1265   -1.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9656   -1.0487   -1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1973    0.9407   -0.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4611   -1.2135    0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8630    0.1227    1.2134 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7139   -0.0192    3.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3287    0.1578    2.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0919    1.3982   -0.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0600   -0.4480   -1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3089    0.0604    0.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5109    1.2602   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3400   -0.1652   -1.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6293   -1.5923   -0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8253    0.8033   -1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3585   -0.7857   -2.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8443   -1.2906   -0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424   -1.9608   -1.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6969    1.8605    0.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6406    0.3461    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0500    1.1726   -0.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5209   -1.3208    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8428   -2.1120    1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4872    0.9904    1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10 12  1  0
  9 10  1  6
  9 13  1  0
 13 14  1  0
 14  2  1  0
  2  1  2  3
  2  3  1  0
  3  8  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
 14  9  1  0
  8  9  1  0
 11 24  1  0
 11 25  1  0
 11 26  1  0
 10 23  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  6
  1 15  1  0
  1 16  1  0
  3 17  1  6
  8 21  1  0
  8 22  1  0
  6 18  1  0
  6 19  1  0
  6 20  1  0
M  END


  Mrv1652309032215052D          

 14 15  0  0  1  0            999 V2000
    1.0396   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3356    1.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1494    2.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1560    1.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0945    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3320   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0945   -1.0164    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
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0175581

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@]12CC1C(=C)[C@H](C2)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O2/c1-7(2)12-5-10(12)8(3)11(6-12)14-9(4)13/h7,10-11H,3,5-6H2,1-2,4H3/t10?,11-,12+/m0/s1

> <INCHI_KEY>
PBWRFXQNNGSAQG-GLXQMMQGSA-N

> <FORMULA>
C12H18O2

> <MOLECULAR_WEIGHT>
194.274

> <EXACT_MASS>
194.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
22.14103805775746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-yl acetate

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
2.06990946

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.013895311208607

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
54.31680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       1.941  -1.941   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.626   2.947   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.279   4.193   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.158   3.108   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.910   0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.220  -0.564   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.910  -1.897   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3    5                                                       
CONECT    5    4    3    6    9                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
trans-Sabinyl acetic acid	Generator

Chemical Formula

C₁₂H₁₈O₂

Average Mass

194.2740 Da

Monoisotopic Mass

194.13068 Da

IUPAC Name

(1R,3S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-yl acetate

Traditional Name

(1R,3S)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)[C@]12CC1C(=C)[C@H](C2)OC(C)=O

InChI Identifier

InChI=1S/C12H18O2/c1-7(2)12-5-10(12)8(3)11(6-12)14-9(4)13/h7,10-11H,3,5-6H2,1-2,4H3/t10?,11-,12+/m0/s1

InChI Key

PBWRFXQNNGSAQG-GLXQMMQGSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Daucus carota	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Thujane monoterpenoid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.94	ALOGPS
logP	2.07	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.32 m³·mol⁻¹	ChemAxon
Polarizability	22.14 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

Not Available

Chemspider ID

4935655

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6430313

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sampietro DA, Lizarraga EF, Ibatayev ZA, Omarova AB, Suleimen YM, Catalan CA: Chemical composition and antimicrobial activity of essential oils from Acantholippia deserticola, Artemisia proceriformis, Achillea micrantha and Libanotis buchtormensis against phytopathogenic bacteria and fungi. Nat Prod Res. 2016 Sep;30(17):1950-5. doi: 10.1080/14786419.2015.1091453. Epub 2015 Sep 24. [PubMed:26404704 ]
Dosoky NS, Setzer WN: Maternal Reproductive Toxicity of Some Essential Oils and Their Constituents. Int J Mol Sci. 2021 Feb 27;22(5):2380. doi: 10.3390/ijms22052380. [PubMed:33673548 ]
Younsi F, Rahali N, Mehdi S, Boussaid M, Messaoud C: Relationship between chemotypic and genetic diversity of natural populations of Artemisia herba-alba Asso growing wild in Tunisia. Phytochemistry. 2018 Apr;148:48-56. doi: 10.1016/j.phytochem.2018.01.014. Epub 2018 Feb 6. [PubMed:29421510 ]
Younsi F, Mehdi S, Aissi O, Rahali N, Jaouadi R, Boussaid M, Messaoud C: Essential Oil Variability in Natural Populations of Artemisia campestris (L.) and Artemisia herba-alba (Asso) and Incidence on Antiacetylcholinesterase and Antioxidant Activities. Chem Biodivers. 2017 Jul;14(7). doi: 10.1002/cbdv.201700017. Epub 2017 Jun 15. [PubMed:28488391 ]
Monzote L, Pinon A, Sculli R, Setzer WN: Chemistry and leishmanicidal activity of the essential oil from Artemisia absinthium from Cuba. Nat Prod Commun. 2014 Dec;9(12):1799-804. [PubMed:25632489 ]
LOTUS database [Link]

Showing NP-Card for (1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate (NP0175581)

MOL for NP0175581 ((1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate)

3D MOL for NP0175581 ((1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate)

3D SDF for NP0175581 ((1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate)

3D-SDF for NP0175581 ((1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate)

PDB for NP0175581 ((1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate)

3D PDB for NP0175581 ((1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate)

SMILES for NP0175581 ((1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate)

INCHI for NP0175581 ((1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate)

Structure for NP0175581 ((1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate)

3D Structure for NP0175581 ((1r,3s)-1-isopropyl-4-methylidenebicyclo[3.1.0]hexan-3-yl acetate)