NP-MRD: Showing NP-Card for 2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid (NP0150849)

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Record Information

Version

2.0

Created at

2022-09-02 07:04:21 UTC

Updated at

2022-09-02 07:04:21 UTC

NP-MRD ID

NP0150849

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid

Description

Alpha-Epoxydihydroartemisinic acid, also known as α-epoxydihydroartemisinate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid is found in Artemisia annua. Alpha-Epoxydihydroartemisinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -2.0422    2.9865    0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8678    2.1615   -0.2164 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4287    2.6851    0.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2547    1.4995    0.7913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3006    0.4271   -0.2890 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3892   -0.5263    0.0583 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5482   -1.6720   -0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7130    0.1226    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8557    1.2702   -0.3441 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7990   -0.5359    0.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0477   -0.1304   -0.5257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2844   -1.5518   -0.1663 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8643   -2.4165   -1.2059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -1.9853   -0.0165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9266   -3.2012    0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610   -1.0986   -0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4903    0.3734   -0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1203    0.7227    0.1660 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7186    4.0646    0.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219    2.7870   -0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2928    2.7283    1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    2.2065   -1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2025    3.2801    1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817    3.2851   -0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221    1.8532    1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7695    1.0727    1.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6785    0.9940   -1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2087   -0.9161    1.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7390   -1.7425   -1.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4856   -1.5670   -1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.5878   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0622   -1.4640    0.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2836   -0.0184   -1.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946   -2.1391    0.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9769   -3.7469    1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6724   -3.8718    0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3533   -2.8622    1.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1391   -1.4027   -1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -1.3380    0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2248    0.8793    0.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6449    0.7963   -1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1312    0.5786    1.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2 18  1  0
 18 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  1  1
 14 13  1  0
 13 12  1  0
 12 11  1  0
  6  8  1  0
  8 10  1  0
  8  9  2  0
 11  5  1  0
 11 18  1  0
 12 14  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  6 28  1  1
  5 27  1  6
  4 25  1  0
  4 26  1  0
  3 23  1  0
  3 24  1  0
  2 22  1  6
  1 19  1  0
  1 20  1  0
  1 21  1  0
 18 42  1  1
 17 40  1  0
 17 41  1  0
 16 38  1  0
 16 39  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 12 34  1  1
 11 33  1  6
 10 32  1  0
M  END


  Mrv1533004231520362D          

 18 20  0  0  0  0            999 V2000
    2.9041   -2.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0846   -2.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7568   -1.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9372   -1.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6094   -0.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011   -0.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7733    0.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9207   -0.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124    0.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2320    0.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5598   -0.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3169   -0.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8876   -1.1089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0681   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2485   -0.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5929   -3.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9207   -3.7587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7733   -2.9069    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
  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
  8 15  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150849

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C1CCC(C)C2CCC3(C)OC3C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O3/c1-8-4-5-11(9(2)14(16)17)12-10(8)6-7-15(3)13(12)18-15/h8-13H,4-7H2,1-3H3,(H,16,17)

> <INCHI_KEY>
FRUVDMZCZGVCDC-UHFFFAOYSA-N

> <FORMULA>
C15H24O3

> <MOLECULAR_WEIGHT>
252.354

> <EXACT_MASS>
252.172544633

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.660275708977615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{5,7a-dimethyl-decahydronaphtho[1,2-b]oxiren-2-yl}propanoic acid

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
2.966824817666666

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.707860115028319

> <JCHEM_PKA_STRONGEST_BASIC>
-4.226553972215423

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
68.1232

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{5,7a-dimethyl-octahydro-1aH-naphtho[1,2-b]oxiren-2-yl}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       5.421  -4.543   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.891  -4.366   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.279  -2.953   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.749  -2.777   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.138  -1.363   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.055  -0.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.443   1.286   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.585  -0.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.503   0.933   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.033   0.756   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.645  -0.657   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.058  -0.045   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.257  -2.070   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.727  -1.893   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.197  -1.717   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.973  -5.603   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.585  -7.016   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.443  -5.426   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   11   15                                                  
CONECT   15   14    3    8                                                  
CONECT   16    2   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
a-Epoxydihydroartemisinate	Generator
a-Epoxydihydroartemisinic acid	Generator
alpha-Epoxydihydroartemisinate	Generator
Α-epoxydihydroartemisinate	Generator
Α-epoxydihydroartemisinic acid	Generator
2-{1a,4-dimethyl-decahydronaphtho[1,2-b]oxiren-7-yl}propanoate	Generator

Chemical Formula

C₁₅H₂₄O₃

Average Mass

252.3540 Da

Monoisotopic Mass

252.17254 Da

IUPAC Name

2-{5,7a-dimethyl-decahydronaphtho[1,2-b]oxiren-2-yl}propanoic acid

Traditional Name

2-{5,7a-dimethyl-octahydro-1aH-naphtho[1,2-b]oxiren-2-yl}propanoic acid

CAS Registry Number

Not Available

SMILES

CC(C1CCC(C)C2CCC3(C)OC3C12)C(O)=O

InChI Identifier

InChI=1S/C15H24O3/c1-8-4-5-11(9(2)14(16)17)12-10(8)6-7-15(3)13(12)18-15/h8-13H,4-7H2,1-3H3,(H,16,17)

InChI Key

FRUVDMZCZGVCDC-UHFFFAOYSA-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
Artemisia annua	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Oxepane
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
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	2.55	ALOGPS
logP	2.97	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.71	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.12 m³·mol⁻¹	ChemAxon
Polarizability	28.66 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

Not Available

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

73797653

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid (NP0150849)

MOL for NP0150849 (2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid)

3D MOL for NP0150849 (2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid)

3D SDF for NP0150849 (2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid)

3D-SDF for NP0150849 (2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid)

PDB for NP0150849 (2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid)

3D PDB for NP0150849 (2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid)

SMILES for NP0150849 (2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid)

INCHI for NP0150849 (2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid)

Structure for NP0150849 (2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid)

3D Structure for NP0150849 (2-{1a,4-dimethyl-octahydro-2h-naphtho[1,2-b]oxiren-7-yl}propanoic acid)