(-)-vernolic acid (CHEBI:38300)

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CHEBI:38300 - (−)-vernolic acid

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ChEBI Name	(−)-vernolic acid

ChEBI ID	CHEBI:38300

ChEBI ASCII Name	(-)-vernolic acid

Definition	An optically active form of vernolic acid having (12R,13S)-configuration.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ZINC000003869735

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

T25 - Ideal conformer

Mrv1927 03092315253D

starting HoverWatcher_5

Time for openFile(T25 - Ideal conformer

Mrv1927 03092315253D

53 53 0 0 0 0 999 V2000

7.9270 0.3530 0.9000 O 0 0 0 0 0 0 0 0 0 0 0 0

7.5810 1.2610 0.1810 C 0 0 0 0 0 0 0 0 0 0 0 0

8.4430 2.2460 -0.1180 O 0 0 0 0 0 0 0 0 0 0 0 0

6.1850 1.2840 -0.3850 C 0 0 1 0 0 0 0 0 0 0 0 0

5.4170 0.0530 0.1020 C 0 0 1 0 0 0 0 0 0 0 0 0

3.9990 0.0760 -0.4720 C 0 0 1 0 0 0 0 0 0 0 0 0

3.2310 -1.1550 0.0150 C 0 0 1 0 0 0 0 0 0 0 0 0

1.8140 -1.1320 -0.5600 C 0 0 1 0 0 0 0 0 0 0 0 0

1.0460 -2.3620 -0.0730 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.3720 -2.3390 -0.6470 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.1280 -3.5510 -0.1680 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.2980 -3.4100 0.4050 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.9640 -2.0580 0.4330 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.3760 -2.1740 -0.1460 C 0 0 1 0 0 0 0 0 0 0 0 0

-5.4740 -1.8420 0.7060 O 0 0 0 0 0 0 0 0 0 0 0 0

-5.1840 -0.8860 -0.3170 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.5260 0.4300 0.1030 C 0 0 1 0 0 0 0 0 0 0 0 0

-5.4440 1.5980 -0.2620 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.7850 2.9140 0.1570 C 0 0 1 0 0 0 0 0 0 0 0 0

-5.7030 4.0820 -0.2080 C 0 0 1 0 0 0 0 0 0 0 0 0

-5.0450 5.3980 0.2120 C 0 0 0 0 0 0 0 0 0 0 0 0

9.3280 2.1860 0.2650 H 0 0 0 0 0 0 0 0 0 0 0 0

5.6720 2.1860 -0.0520 H 0 0 0 0 0 0 0 0 0 0 0 0

6.2330 1.2740 -1.4740 H 0 0 0 0 0 0 0 0 0 0 0 0

5.9290 -0.8500 -0.2310 H 0 0 0 0 0 0 0 0 0 0 0 0

5.3680 0.0620 1.1910 H 0 0 0 0 0 0 0 0 0 0 0 0

3.4870 0.9790 -0.1390 H 0 0 0 0 0 0 0 0 0 0 0 0

4.0480 0.0670 -1.5610 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7430 -2.0570 -0.3180 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1830 -1.1450 1.1040 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3010 -0.2290 -0.2270 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8620 -1.1410 -1.6490 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5580 -3.2650 -0.4060 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9970 -2.3530 1.0160 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8840 -1.4360 -0.3140 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3230 -2.3490 -1.7360 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.7060 -4.5370 -0.2960 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7840 -4.2610 0.8570 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0210 -1.7020 1.4610 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3840 -1.3550 -0.1640 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.5230 -2.9670 -0.8790 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.8690 -0.8250 -1.1630 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.3560 0.4240 1.1790 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.5730 0.5400 -0.4150 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.6140 1.6040 -1.3390 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.3970 1.4870 0.2560 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.6150 2.9080 1.2340 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.8330 3.0250 -0.3610 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.8730 4.0880 -1.2840 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.6560 3.9720 0.3100 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.0920 5.5090 -0.3060 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.6990 6.2310 -0.0480 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.8750 5.3920 1.2880 H 0 0 0 0 0 0 0 0 0 0 0 0

4 5 1 0 0 0 0

4 2 1 0 0 0 0

5 6 1 0 0 0 0

7 6 1 0 0 0 0

7 8 1 0 0 0 0

2 1 2 0 0 0 0

2 3 1 0 0 0 0

8 9 1 0 0 0 0

21 20 1 0 0 0 0

9 10 1 0 0 0 0

20 19 1 0 0 0 0

10 11 1 0 0 0 0

19 18 1 0 0 0 0

11 12 2 0 0 0 0

18 17 1 0 0 0 0

13 12 1 0 0 0 0

13 14 1 0 0 0 0

17 16 1 0 0 0 0

14 16 1 0 0 0 0

14 15 1 0 0 0 0

16 15 1 0 0 0 0

3 22 1 0 0 0 0

4 23 1 0 0 0 0

4 24 1 0 0 0 0

5 25 1 0 0 0 0

5 26 1 0 0 0 0

6 27 1 0 0 0 0

6 28 1 0 0 0 0

7 29 1 0 0 0 0

7 30 1 0 0 0 0

8 31 1 0 0 0 0

8 32 1 0 0 0 0

9 33 1 0 0 0 0

9 34 1 0 0 0 0

10 35 1 0 0 0 0

10 36 1 0 0 0 0

11 37 1 0 0 0 0

12 38 1 0 0 0 0

13 39 1 0 0 0 0

13 40 1 0 0 0 0

14 41 1 6 0 0 0

16 42 1 6 0 0 0

17 43 1 0 0 0 0

17 44 1 0 0 0 0

18 45 1 0 0 0 0

18 46 1 0 0 0 0

19 47 1 0 0 0 0

19 48 1 0 0 0 0

20 49 1 0 0 0 0

20 50 1 0 0 0 0

21 51 1 0 0 0 0

21 52 1 0 0 0 0

21 53 1 0 0 0 0

M END): 23 ms

reading 53 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

53 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Formula

C18H32O3

Net Charge

Average Mass

296.451

Monoisotopic Mass

296.23514

InChI

InChI=1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m0/s1

InChIKey

CCPPLLJZDQAOHD-BEBBCNLGSA-N

SMILES

CCCCC[C@@H]1O[C@@H]1C\C=C/CCCCCCCC(O)=O

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. (via vernolic acid ) metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via epoxyoctadecenoic acid )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	(−)-vernolic acid (CHEBI:38300) is a vernolic acid (CHEBI:38299) (−)-vernolic acid (CHEBI:38300) is conjugate acid of (−)-vernolate (CHEBI:194416) (−)-vernolic acid (CHEBI:38300) is enantiomer of (+)-vernolic acid (CHEBI:27706)

Incoming	(−)-vernolate (CHEBI:194416) is conjugate base of (−)-vernolic acid (CHEBI:38300) (+)-vernolic acid (CHEBI:27706) is enantiomer of (−)-vernolic acid (CHEBI:38300)

IUPAC Name

(9Z)-11-[(2R,3S)-3-pentyloxiran-2-yl]undec-9-enoic acid

Synonyms	Sources
(−)-12(R),13(S)-vernolic acid	ChEBI
(−)-leukotoxin B	ChEBI
(−)-Vernolsäure	ChEBI
(12R,13S)-(9Z)-12,13-Epoxyoctadecenoic acid	KEGG COMPOUND
(9Z)-(12R,13S)-12,13-epoxyoctadecenoic acid	ChEBI
12,13-epoxylinoleic acid	ChEBI
cis-12,13-Epoxy-cis-9-octadecenoic acid	KEGG COMPOUND
cis-12S,13R,-ep, 9c-18:1	ChEBI
Vernolic acid	KEGG COMPOUND

Manual Xrefs	Databases
C00001241	KNApSAcK
C08368	KEGG COMPOUND
C14826	KEGG COMPOUND
T25	PDBeChem
View more database links

Registry Numbers	Types	Sources
503-07-1	CAS Registry Number	KEGG COMPOUND
86881	Reaxys Registry Number	Reaxys

Citations

Lee DS, Nioche P, Hamberg M, Raman CS (2008)
Structural insights into the evolutionary paths of oxylipin biosynthetic enzymes.
Nature 455, 363-368 [PubMed:18716621]
[show Abstract]

Blee E, Ståhl U, Schuber F, Stymne S (1993)
Regio- and stereoselectivity of cytochrome P-450 and peroxygenase-dependent formation of cis-12,13-epoxy-9(Z)-octadecenoic acid (vernolic acid) in Euphorbia lagascae.
Biochemical and biophysical research communications 197, 778-784 [PubMed:8267615]
[show Abstract]

Last Modified

09 March 2023

CHEBI:38300 - (−)-vernolic acid

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