Violaxanthin

  • GreenMolBD CID : 1838
  • Molecular Formula : C40H56O4
  • Molecular Weight : 600.884
  • Exact Molecular Mass : 600.418
  • IUPAC Name : (1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,3S,6S)-3-hydroxy-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-6-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
  • InChI : InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,37+,38+,39-,40-/m0/s1
  • InChI Key : SZCBXWMUOPQSOX-WVJDLNGLSA-N
  • Canonical SMILES : CC(=CC=CC=C(C)C=CC=C(C)C=CC12C(CC(CC1(O2)C)O)(C)C)C=CC=C(C)C=CC34C(CC(CC3(O4)C)O)(C)C
  • Isomeric SMILES : C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C12OC1(CC(CC2(C)C)O)C)/C)/C)/C=C/C=C(/C=C/C34OC3(CC(CC4(C)C)O)C)\C
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

1.2. Taxonomy Tree

1.3. Alternative Parent

Oxepanes; Secondary alcohols; Cyclic alcohols and derivatives; Oxacyclic compounds; Epoxides; Dialkyl ethers; Hydrocarbon derivatives;

1.4. Molecular Framework

Aliphatic heteropolycyclic compounds

1.5. Substituents

Xanthophyll; Oxepane; Cyclic alcohol; Secondary alcohol; Oxacycle; Organoheterocyclic compound; Ether; Oxirane; Dialkyl ether; Organic oxygen compound; Hydrocarbon derivative; Organooxygen compound; Alcohol; Aliphatic heteropolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
8.9698 65.52 2 4 44 10 0 0 18.3214 920.731 684.016 0.652616

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-132.749832 1.3 -4.541 -8.21886 -0.86337 3.678

4. Compound Reactivity

DLP nRFG nLMR
9 2 7

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Carcinogen Non-Mutagen Toxic 1.92767 447.818 0.000532049 Mild Weak None Degradable 8.40E-6 0.0558161

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
No No No Yes Yes Yes Yes

7. Synonyms

Name
Violaxanthin
Zeaxanthin diepoxide
all-trans-Violaxanthin
trans-Violaxanthin
126-29-4
(3S,5R,6S,3'S,5'R,6'S)-5,6,5',6'-DIEPOXY-5,6,5',6'- TETRAHYDRO-BETA,BETA-CAROTENE-3,3'-DIOL
(3S,5R,6S,3'S,5'R,6'S)-5,6,5',6'-DIEPOXY-5,6,5',6'-TETRAHYDRO-BETA,BETA-CAROTENE-3,3'-DIOL
XAT
UNII-51C926029A
Zeaxanthin diepoxidl
(9Z)-Violaxanthin
13-cis-Violaxanthin
all-trans-Violaxanthil
AC1L9LYN
SCHEMBL97720
E161e
CHEBI:35288
E 161e
SZCBXWMUOPQSOX-WVJDLNGLSA-N
ZINC8221270
Violaxanthin, >=90.0% (HPLC)
5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-beta-carotene-3,3'-diol
LMPR01070282
DB03460
HE017353
LP070833
51C926029A
C08614
09958A8F-4AFE-43DB-9034-C562F62D8ABD
5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-|A-carotene-3,3'-diol
5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-beta,beta-carotene-3,3'-diol
(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,3S,6S)-3-hydroxy-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-6-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
(3S,3'S,5R,5'R, 6S,6'S)-5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene-3,3'-diol
(3S,3'S,5R,5'R,6S,6'S)-5,5',6,6'-tetrahydro-5,6:5',6'-diepoxy-beta,beta-carotene-3,3'-diol
(3S,3'S,5R,5'R,6S,6'S)-5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene-3,3'-diol
26927-07-1

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Violaxanthin
Commelina benghalensis L Leaf 2
Coriandrum sativum Linn. Leaf; Shoot 28
Sesbania grandiflora Leaf 2

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
3632404441717 CheMall CorporationSource URLSource DetailBG08061015Source Record URL
104639443ABI ChemSource URLSource DetailAC1L9LYNSource Record URL
329757838Sigma-AldrichSource URLSource Detail52444_SIGMASource Record URL
348671140Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0189291Source Record URL
162224438Chembase.cnSource URLSource Detail130154Source Record URL
355433433MuseChemSource URLSource DetailM068319Source Record URL
57404869NovoSeekSource URLSource Detail448438Source Record URL
7891116SMIDSource URLSource DetailXATSource Record URL
258473480ZINCSource URLSource DetailZINC8221270Source Record URL