Eugenol

  • GreenMolBD CID : 70
  • Molecular Formula : C10H12O2
  • Molecular Weight : 164.204
  • Exact Molecular Mass : 164.084
  • IUPAC Name : 2-methoxy-4-prop-2-enylphenol
  • InChI : InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
  • InChI Key : RRAFCDWBNXTKKO-UHFFFAOYSA-N
  • Canonical SMILES : COC1=C(C=CC(=C1)CC=C)O
  • Isomeric SMILES : COc1cc(ccc1O)CC=C
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

1.2. Taxonomy Tree

1.3. Alternative Parent

Phenoxy compounds; Methoxybenzenes; Anisoles; Alkyl aryl ethers; 1-hydroxy-2-unsubstituted benzenoids; Hydrocarbon derivatives;

1.4. Molecular Framework

Aromatic homomonocyclic compounds

1.5. Substituents

Methoxyphenol; Phenoxy compound; Methoxybenzene; Phenol ether; Anisole; 1-hydroxy-2-unsubstituted benzenoid; Alkyl aryl ether; Monocyclic benzene moiety; Ether; Organic oxygen compound; Hydrocarbon derivative; Organooxygen compound; Aromatic homomonocyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
2.12927 29.46 1 2 12 3 6 6 4.85598 239.869 191.66 0.684558

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-47.490033 1.09 -4.202 -8.62922 0.22609 4.428

4. Compound Reactivity

DLP nRFG nLMR
2 0 3

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)
Non-Carcinogen Non-Mutagen Toxic 1.42347 10713 0.0715145 Moderate Strong Severe Degradable 0.000767306 5.4845

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes Yes Yes Yes Yes Yes

7. Synonyms

Name
eugenol
97-53-0
4-Allyl-2-methoxyphenol
4-Allylguaiacol
Eugenic acid
Allylguaiacol
Caryophyllic acid
p-Allylguaiacol
p-Eugenol
2-Methoxy-4-prop-2-enylphenol
2-Methoxy-4-allylphenol
Engenol
1,3,4-Eugenol
4-Allylcatechol-2-methyl ether
2-Methoxy-4-(2-propenyl)phenol
Synthetic eugenol
Phenol, 2-methoxy-4-(2-propenyl)-
1-Hydroxy-2-methoxy-4-allylbenzene
2-Methoxy-1-hydroxy-4-allylbenzene
4-Allyl-1-hydroxy-2-methoxybenzene
5-Allylguaiacol
1-Hydroxy-2-methoxy-4-prop-2-enylbenzene
Eugenol (natural)
4-Hydroxy-3-methoxy-1-allylbenzene
2-Hydroxy-5-allylanisole
4-Hydroxy-3-methoxyallylbenzene
2-methoxy-4-(prop-2-en-1-yl)phenol
Phenol, 4-allyl-2-methoxy-
2-Methoxy-4-(2-propen-1-yl)phenol
Eugenol [USAN]
NCI-C50453
1-allyl-4-hydroxy-3-methoxybenzene
1-Allyl-3-methoxy-4-hydroxybenzene
FEMA No. 2467
4-Allylcatechol 2-methyl ether
Caswell No. 456BC
FEMA Number 2467
2-Metoksy-4-allilofenol
FA 100
CCRIS 306
Eugenol [USP]
NSC 209525
UNII-3T8H1794QW
CHEBI:4917
HSDB 210
2-Metoksy-4-allilofenol [Polish]
EINECS 202-589-1
EPA Pesticide Chemical Code 102701
BRN 1366759
CHEMBL42710
Phenol, 2-methoxy-4-(2-propen-1-yl)-
AI3-00086
2-Methoxy-4-(3-propenyl)phenol
RRAFCDWBNXTKKO-UHFFFAOYSA-N
Eugenol (USP)
MFCD00008654
4-Allyl-1-Hydroxy-2-Methoxy Benzene
NCGC00091449-05
DSSTox_CID_617
DSSTox_RID_75693
DSSTox_GSID_20617
WLN: 1U2R DQ CO1
2-Methoxy-4-[2-propenyl]phenol
CAS-97-53-0
bioxeda
dentogum
Eugenolum
Eugenol Special
4-Allylguaicol
Caryophyllic ac id
4-allyl-2methoxyphenol
3s0e
AC1L1FNK
Spectrum2_001264
Spectrum3_000646
Spectrum4_001783
Spectrum5_000425
ACMC-1AOH6
4-allyl-2-methoxy-Phenol
bmse010053
D0O4QB
Epitope ID:114091
Eugenol, puriss., 98%
AC1Q7AE5
SCHEMBL20361
BSPBio_002251
Eugenol, 99% 100g
KBioGR_002327
KSC486Q8H
MLS000028901
BIDD:ER0696
Bio-0581
DivK1c_000692
SPECTRUM1500296
SPBio_001228
AC1Q46B0
GTPL2425
ZINC1411
DTXSID9020617
CTK3I6883
HMS502C14
KBio1_000692
KBio3_001471
Eugenol, ReagentPlus(R), 99%
NSC8895
4-(2-Propenyl)-2-methoxyphenol
Eugenol, natural, >=98%, FG
MolPort-001-783-095
NINDS_000692
3T8H1794QW
Eugenol, >=98%, FCC, FG
HMS1920O08
HMS2091F09
Pharmakon1600-01500296
HY-N0337
KS-00000WP5
NSC-8895
1-hydroxy-4-allyl-2-methoxybenzene
Tox21_111134
Tox21_202040
Tox21_300105
ANW-40868
BBL027721
BDBM50164168
CCG-38827
NSC209525
NSC757030
s4706
SBB012362
STL371304
4 -allyl-1-hydroxy-2-methoxybenzene
Eugenol, tested according to Ph.Eur.
3-(3-methoxy-4-hydroxyphenyl)propene
AKOS000121354
Tox21_111134_1
CS-7807
DB09086
FS-2702
LS-2027
NSC-209525
NSC-757030
RTR-038621
SDCCGMLS-0066578.P001
1-hydroxy-2-methoxy-4-propenylbenze ne
IDI1_000692
NCGC00091449-01
NCGC00091449-02
NCGC00091449-03
NCGC00091449-04
NCGC00091449-06
NCGC00091449-07
NCGC00091449-08
NCGC00091449-10
NCGC00253915-01
NCGC00259589-01
AK307784
BC682398
BT000195
CJ-00049
Eugenol, Vetec(TM) reagent grade, 98%
K753
KB-51837
OR042429
OR381701
SMR000059114
ST069318
SBI-0051381.P003
Eugenol, PESTANAL(R), analytical standard
TR-038621
A0232
FT-0615974
N1805
C10453
D04117
AB00051992_02
Eugenol, primary pharmaceutical reference standard
SR-05000002043
Eugenol, certified reference material, TraceCERT(R)
I01-7260
I01-8770
Q-201105
SR-05000002043-2
BRD-K32977963-001-01-9
Eugenol, European Pharmacopoeia (EP) Reference Standard
F0001-2306
2-methoxy-4-(prop-2-en-1-yl)phenol4-allyl-2-methoxyphenol
Eugenol, United States Pharmacopeia (USP) Reference Standard
Eugenol, pharmaceutical secondary standard
traceability to USP and PhEur
InChI=1/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H
EOL

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Eugenol
Abelmoschus esculentus (L.) Moench Pod 3
Abutilon indicum (L.) Sw. Root 5 , 9
Ageratum conyzoides L Leaf; Aerial 1 , 2 , 17
Anisomeles indica (L.) Kuntze. Aerial 6
Cocos nucifera L. Fiber 1
Coriandrum sativum Linn. Seed; Fruit; Root 2 , 3 , 7 , 12 , 13 , 17 , 33
Cuscuta reflexa Whole Plant 2
Dodonaea viscosa (L.) Jacq. Stem 6
Helianthus annuus Flower 8
Jasminum graniflorum Flower 3 , 4 , 5 , 20
Jasminum sambac L. Flower 7
Juglans regia Leaf; Fruit 14 , 15 , 17
Lantana camara L Aerial; Leaf and Flower 2 , 3
Leucas aspera Aerial 3
Lippia nodiflora (L.) Pod 2
Mangifera indica Fruit 7
Mentha arvensis Leaf; Aerial 1 , 7
Rhizophora apiculata 8
Rosa damascena Petal; Flower 1 , 4 , 6 , 7 , 11 , 13 , 14
Tamarindus indica Fruit 9
Viola odorata Leaf 7

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
109 15-Lipoxygenase (SLO) 3S0E 34100 10.3109/14756366.2010.495717 20939767
69 aldehyde dehydrogenase 1 family member A1 ALDH1A1 Homo sapiens 14.1254 1030
56 androgen receptor Homo sapiens 3S0E 19000 10.1016/j.bmcl.2010.02.059 20226658
56 androgen receptor AR Homo sapiens 19 473864
56 androgen receptor AR Homo sapiens 50.1187 588516
110 apolipoprotein B mRNA editing enzyme catalytic subunit 3G APOBEC3G Homo sapiens 33.4983 588379
111 Chorismate mutase (MTB CM) 3S0E 2.86E+4
52 C-X-C motif chemokine ligand 8 CXCL8 Homo sapiens 66.8242 651758
112 Cyclooxygenase Homo sapiens 3S0E 129000 12444669
112 Cyclooxygenase Homo sapiens 3S0E 129000 10.1021/np049655u 16038536
113 Cyclooxygenase-1 (COX-1) 3S0E 11000 10.1021/np049655u 16038536
114 cytochrome P450 family 3 subfamily A member 4 CYP3A4 Homo sapiens 3.9811 884
114 cytochrome P450 family 3 subfamily A member 4 CYP3A4 Homo sapiens 3.9811 885
57 estrogen receptor 1 ESR1 Homo sapiens 0.0866 743075
57 estrogen receptor 1 ESR1 Homo sapiens 0.109005 743077
57 estrogen receptor 1 ESR1 Homo sapiens 0.154 743069
57 estrogen receptor 1 ESR1 Homo sapiens 43.6412 743069
84 geminin, DNA replication inhibitor GMNN Homo sapiens 13.3359 624297
85 Jun proto-oncogene, AP-1 transcription factor subunit JUN Homo sapiens 0.0013 1159526
30 nuclear factor, erythroid 2 like 2 NFE2L2 Homo sapiens 26.6011 743219
30 nuclear factor, erythroid 2 like 2 NFE2L2 Homo sapiens 76.4895 743202
80 nuclear receptor subfamily 1 group I member 3 NR1I3 Homo sapiens 22.8175 1224893
80 nuclear receptor subfamily 1 group I member 3 NR1I3 Homo sapiens 33.4915 1224838
55 nuclear receptor subfamily 3 group C member 1 NR3C1 Homo sapiens 10.6822 720691
31 peripheral myelin protein 22 Pmp22 Rattus norvegicus 0.4053 624032
81 tumor protein p53 TP53 Homo sapiens 27.1395 651631
64 vitamin D receptor VDR Homo sapiens 0.1949 743223

10. Chemical Vendors

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354325206iChemical Technology USA IncSource URLSource DetailEBD646149Source Record URL
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329891355AvaChem ScientificSource URLSource Detail3623Source Record URL
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329749822Sigma-AldrichSource URLSource Detail1268965_USPSource Record URL
329755246Sigma-AldrichSource URLSource Detail35995_SIALSource Record URL
329757078Sigma-AldrichSource URLSource Detail46129_SIALSource Record URL
329768681Sigma-AldrichSource URLSource Detail79891_SIALSource Record URL
329799063Sigma-AldrichSource URLSource DetailE5000000_SIALSource Record URL
24894609Sigma-AldrichSource URLSource DetailE51791_ALDRICHSource Record URL
329823265Sigma-AldrichSource URLSource DetailPHR1269_SIALSource Record URL
329828536Sigma-AldrichSource URLSource DetailV001263_VETECSource Record URL
329829436Sigma-AldrichSource URLSource DetailV900001_VETECSource Record URL
24901114Sigma-AldrichSource URLSource DetailW246700_ALDRICHSource Record URL
24901115Sigma-AldrichSource URLSource DetailW246719_ALDRICHSource Record URL
355036086MuseChemSource URLSource DetailR016360Source Record URL
162155573Nanjing KaimuboSource URLSource DetailKB-51837Source Record URL
204372645TractusSource URLSource DetailRTR-038621Source Record URL
135559081TractusSource URLSource DetailTR-038621Source Record URL
196110577BoerchemSource URLSource DetailBC682398Source Record URL
340097045BePharm Ltd.Source URLSource DetailB129899Source Record URL
143401459TimTecSource URLSource DetailSBB012362Source Record URL
124570895TimTecSource URLSource DetailST069318Source Record URL
310272988Glentham Life Sciences Ltd.Source URLSource DetailGK9909Source Record URL
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184014592Vitas-M LaboratorySource URLSource DetailBBL027721Source Record URL
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99245798ISpharmSource URLSource DetailI01-7260Source Record URL
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255512961ZINCSource URLSource DetailZINC1411Source Record URL
342401284Wubei-BiochemSource URLSource DetailWB000548SUSource Record URL
3562666431717 CheMall CorporationSource URLSource DetailBG00601193Source Record URL
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3604094711717 CheMall CorporationSource URLSource DetailBG07250759Source Record URL
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3133265ChemExper Chemical DirectorySource URLSource DetailHcLD@@iJ[g]xZB@i@@@Source Record URL
254788034Boc SciencesSource URLSource Detail97-53-0Source Record URL
162179262AK Scientific, Inc. (AKSCI)Source URLSource DetailK753Source Record URL
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