(-)-caryophyllene oxide - Compound Card

(-)-caryophyllene oxide

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(-)-caryophyllene oxide

Structure
Zoomed Structure
  • Family: Plantae - Malvaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C=C1CC[C@H]2O[C@@]2(CC[C@@H]2[C@@H]1CC2(C)C)C
InChI InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15-/m1/s1
InChIKey NVEQFIOZRFFVFW-RGCMKSIDSA-N
Formula C15H24O
HBA 1
HBD 0
MW 220.36
Rotatable Bonds 0
TPSA 12.53
LogP 3.94
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 220.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Curcuma longa Zingiberaceae Plantae 136217
2 Chrysanthemum viscidehirtum Asteraceae Plantae 13422
3 Conyza bonariensis Asteraceae Plantae 91242
4 Chrysanthemum macrocarpum Asteraceae Plantae 13422
5 Launaea resedifolia Asteraceae Plantae 43198
6 Mkilua fragrans Annonaceae Plantae 49754
7 Anthemis tigrensis Asteraceae Plantae 158234
8 Plectranthus marrubioides Lamiaceae Plantae 204214
9 Hugonia castaneifolia Liliaceae Plantae 610148
10 Gossypium barbadense Malvaceae Plantae 3634

Showing of synonyms

  • Khallouki F, Hmamouchi MH, et al. (2000). Antibacterial and molluscicidal activities of the essential oil of Chrysanthemum viscidehirtum. Fitoterapia,2000,71,544-546. [View] [PubMed]
  • Baraza LD, Joseph CC, et al. (2008). Antifungal rosane diterpenes and other constituents of Hugonia castaneifolia.. Phytochemistry,2008,69(1),200-205. [View] [PubMed]
  • Baraza LD, Nkunya MH, et al. (2006). C18 tetraynoic fatty acids and essential oil composition of Mkilua fragrans. Natural Product Research,2006,20(2),187-193. [View] [PubMed]
  • Zellagui A, Gherraf N, et al. (2012). Chemical composition and antibacterial activity of the essential oils from Launaea resedifolia L.. Organic and Medicinal Chemistry Letters,2012,2(1),2. [View] [PubMed]
  • Mabrouk S, Elaissi A, et al. (2011). Chemical composition of essential oils from leaves, stems, flower heads and roots of Conyza bonariensis L. from Tunisia. Natural Product Research,2011,5(1),77-84. [View] [PubMed]
  • Boutaghane N, Kabouche A, et al. (2008). Composition of the essential oil of Chrysanthemum macrocarpum from Algeria. Chemistry of Natural Compounds,2008,44(6),817-818. [View]
  • El Demerdash A, Dawidar AM, et al. (2012). Gingerdione from the rhizomes of Curcuma longa. Chemistry of Natural Compounds,2012,48(4),646-648. [View]
  • Hedin P, Thompson A, et al. (1972). Malvaceae Egyptian Cotton Leaf Essential Oil. Phytochemistry, 1972, 11(7), 2356-2357. [View]
  • Sorsa A, Asfaw N. (2007). Phytochemical investigation on the aerial part of Anthemis tigreensis (chloroform extract). M.Sc. Thesis-3, Addis Ababa University, Ethiopia, 2007. [View] [PubMed]
  • Omolo MO, Okinyo D, et al. (2004). Repellency of essential oils of some Kenyan plants against Anopheles gambiae. Phytochemistry,2004,65(20),2797-2802. [View] [PubMed]
Pubchem: 1742210
Kegg Ligand: C16908
Chebi: 67818
Nmrshiftdb2: 60019111
Metabolights: MTBLC67818
Bindingdb: 50241720
CPRiL: 30583
Structure

SMILES: C1CC(CC2)C1C(=C)CCC(O3)C23

Level: 0

Mol. Weight: 220.36 g/mol

Antibacterial
Antimicrobial
Molluscicidal
Repellent

Absorption

Caco-2 (logPapp)
-4.94
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.22
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.16
Plasma Protein Binding
33.55
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
17.5
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.8
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.32
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.77
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
1.39
Rat (Acute)
1.41
Rat (Chronic Oral)
1.23
Fathead Minnow
3.94
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
274.99
Hydration Free Energy
-1.68
Log(D) at pH=7.4
3.84
Log(P)
4.56
Log S
-4.34
Log(Vapor Pressure)
-1.66
Melting Point
39.08
pKa Acid
9.44
pKa Basic
6.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9309
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9309
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9074
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9074
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7851
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7851
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7845
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7845
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7754
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7754
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7684
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7684
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7676
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7676
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7648
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7648
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7644
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7644
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7609
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7609
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7585
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7585
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7584
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7584
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7565
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7565
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7544
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7544
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7450
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7450
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7405
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7405
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7397
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7397
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7382
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7382
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7369
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7369
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7335
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7335
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7330
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7330
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7329
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7329
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7324
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7324
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7291
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7291
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7284
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7284
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7277
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7277
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7274
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7274
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7254
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7254
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7204
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7204
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7194
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7194
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7167
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7167
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7143
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7143
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7139
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7139
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7132
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7132
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7102
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7102
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7101
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7101
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7101
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7101
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7096
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7096
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7087
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7087
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7078
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7078
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7076
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7076
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7075
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7075
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7064
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7064
Epoxide hydrolase LasB B6ZK72 LSD19_STRLS Streptomyces lasalocidi 3 0.7058
Epoxide hydrolase LasB B6ZK72 LSD19_STRLS Streptomyces lasalocidi 3 0.7058
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7021
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7021
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7016
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7016
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7004
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7004

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