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Echinenone
- Family: Plantae - Convolvulaceae
- Kingdom: Plantae
- Class: Carotenoid
| Canonical Smiles | C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(C)C(=O)CCC1(C)C)/C)/C)/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C |
|---|---|
| InChI | InChI=1S/C40H54O/c1-30(18-13-20-32(3)23-25-36-34(5)22-15-28-39(36,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-37-35(6)38(41)27-29-40(37,9)10/h11-14,16-21,23-26H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+ |
| InChIKey | QXNWZXMBUKUYMD-QQGJMDNJSA-N |
| Formula | C40H54O |
| HBA | 1 |
| HBD | 0 |
| MW | 550.87 |
| Rotatable Bonds | 10 |
| TPSA | 17.07 |
| LogP | 11.78 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.42 |
| Exact Mass | 550.42 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Convolvulus althaeoides | Convolvulaceae | Plantae | 267570 |
Showing of synonyms
Echinenone
432-68-8
Beta,beta-Caroten-4-one
All-trans-Echinenone
Aphanin
Myoxanthin
LJ5IO02MNQ
Echinenone/ (Myxoxanthin)
.beta.,.beta.-Caroten-4-one
2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-2-en-1-one
Echinenone (Technical Grade)
4-oxo-beta-carotene
UNII-LJ5IO02MNQ
Ss,ss-Caroten-4-one
Myxoxanthine
Echinenon
EINECS 207-083-4
B,b-Caroten-4-one
4-keto-beta-carotene
Echinenone, all-trans-
ECHINENONE [MI]
.BETA.-ECHINENONE
Compound TNP-004859
SCHEMBL114770
CHEBI:4746
4-OXO-.BETA.-CAROTENE
4-KETO-.BETA.-CAROTENE
DTXSID101026555
Echinenone, >=95.0% (HPLC)
.beta.-Caroten-4-one, all-trans-
LMPR01070060
AKOS040734904
FE57771
NS00043351
C08592
ECHINENONE (CONSTITUENT OF SPIRULINA) [DSC]
Q1280339
2,4,4-trimethyl-3-[3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-2-en-1-one
2-Cyclohexen-1-one, 2,4,4-trimethyl-3-[3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,5,7,9,11,13,15,17-octadecanonaenyl]-, (all-E)-
- Hrichi S, Chaabane-Banaoues R, et al. (2020). Effect of seasonal variation on the chemical composition and antioxidant and antifungal activities of Convolvulus althaeoides L. leaf extract. Arabian Journal of Chemistry, 2020, 13(6), 5651-5668. [View]
Pubchem:
5281236
Cas:
432-68-8
Gnps:
CCMSLIB00000205501
Zinc:
ZINC000004097703
Kegg Ligand:
C08592
Chebi:
4746
Nmrshiftdb2:
60065158
Metabolights:
MTBLC4746
Pdb Ligand:
ECH
CPRiL:
156523
SMILES: C1CCC(=O)C=C1C=CC=CC=CC=CC=CC=CC=CC=CC=CC2=CCCCC2
Level: 1
Mol. Weight: 550.87 g/mol
SMILES: O=C1C=CCCC1
Level: 0
Mol. Weight: 550.87 g/mol
SMILES: C1=CCCCC1
Level: 0
Mol. Weight: 550.87 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.58
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.86
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.38
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 2.73
- Plasma Protein Binding
- 88.53
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- -2.27
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.52
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.51
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 7.38
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Toxic
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -2063.47
- Rat (Acute)
- 2.76
- Rat (Chronic Oral)
- 2.46
- Fathead Minnow
- 15.71
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Toxic
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 483.67
- Hydration Free Energy
- -3.02
- Log(D) at pH=7.4
- 6.13
- Log(P)
- 11.13
- Log S
- -7.61
- Log(Vapor Pressure)
- -7.2
- Melting Point
- 176.23
- pKa Acid
- 15.72
- pKa Basic
- 5.48
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.9632 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.9397 |
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.9279 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8997 |
| Bacteriorhodopsin | P02945 | BACR_HALSA | Halobacterium salinarum | 3 | 0.8981 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8869 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8840 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.8787 |
| Cartilage oligomeric matrix protein | P35444 | COMP_RAT | Rattus norvegicus | 3 | 0.8703 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.8683 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.8534 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8283 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8232 |
| Retinol-binding protein 2 | P50120 | RET2_HUMAN | Homo sapiens | 3 | 0.8226 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.8100 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.8066 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 3 | 0.8008 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7868 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7856 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7829 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7814 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7783 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7718 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7709 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7709 |
| Putative cytochrome P450 120 | Q59990 | CP120_SYNY3 | Synechocystis sp | 3 | 0.7706 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 2 | 0.7701 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7682 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7661 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7660 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7649 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7609 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7579 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7553 |
| Oxysterols receptor LXR-beta | P55055 | NR1H2_HUMAN | Homo sapiens | 3 | 0.7542 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7535 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7532 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7513 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7508 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7488 |
| Retinaldehyde-binding protein 1 | P12271 | RLBP1_HUMAN | Homo sapiens | 3 | 0.7472 |
| Nuclear receptor ROR-alpha | P35398 | RORA_HUMAN | Homo sapiens | 3 | 0.7454 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7454 |
| Retinol-binding protein 2 | P06768 | RET2_RAT | Rattus norvegicus | 3 | 0.7450 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7443 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7402 |
| Japanin | M1MR49 | M1MR49_RHIAP | Rhipicephalus appendiculatus | 3 | 0.7393 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7392 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7378 |
| Retinoic acid receptor gamma | P13631 | RARG_HUMAN | Homo sapiens | 3 | 0.7356 |
| Retinol-binding protein 4 | P02753 | RET4_HUMAN | Homo sapiens | 3 | 0.7355 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 2 | 0.7343 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7333 |
| Retinoic acid receptor beta | P10826 | RARB_HUMAN | Homo sapiens | 3 | 0.7325 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7310 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.7305 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.7302 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7297 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7290 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7272 |
| Beta-elicitin cryptogein | P15570 | ELIB_PHYCR | Phytophthora cryptogea | 3 | 0.7269 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.7266 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.7264 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7262 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7232 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 2 | 0.7219 |
| Chloramphenicol acetyltransferase | P62577 | CAT_ECOLX | Escherichia coli | 3 | 0.7216 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 3 | 0.7212 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7202 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7194 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7172 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7161 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.7152 |
| Retinol-binding protein 1 | P09455 | RET1_HUMAN | Homo sapiens | 3 | 0.7146 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7134 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7132 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7118 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7116 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7098 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7096 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7093 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7091 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7084 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7081 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 3 | 0.7078 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.7078 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7069 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7066 |
| Abscisic acid receptor PYL10 | Q8H1R0 | PYL10_ARATH | Arabidopsis thaliana | 3 | 0.7062 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7045 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7040 |
| Endoplasmin, putative | Q8I0V4 | Q8I0V4_PLAF7 | Plasmodium falciparum | 3 | 0.7034 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7015 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7011 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7002 |