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Trans-luteoxanthin
- Family: Plantae - Convolvulaceae
- Kingdom: Plantae
-
Class: Carotenoid
- Subclass: Epoxycarotenol
| Canonical Smiles | C/C(=C\C=C\C=C(\C=C\C=C(\C1C=C2[C@@](O1)(C)C[C@H](CC2(C)C)O)/C)/C)/C=C/C=C(/C=C/[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)\C |
|---|---|
| InChI | InChI=1S/C40H56O4/c1-28(17-13-18-30(3)21-22-40-37(7,8)25-33(42)27-39(40,10)44-40)15-11-12-16-29(2)19-14-20-31(4)34-23-35-36(5,6)24-32(41)26-38(35,9)43-34/h11-23,32-34,41-42H,24-27H2,1-10H3/b12-11+,17-13+,19-14+,22-21+,28-15+,29-16+,30-18+,31-20+/t32-,33-,34?,38+,39+,40-/m0/s1 |
| InChIKey | YNNRPBRNWWIQPQ-MAAFUUECSA-N |
| Formula | C40H56O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 600.88 |
| Rotatable Bonds | 9 |
| TPSA | 62.22 |
| LogP | 8.97 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 44 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.55 |
| Exact Mass | 600.42 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Convolvulus althaeoides | Convolvulaceae | Plantae | 267570 |
Showing of synonyms
Trans-luteoxanthin
Luteoxanthin
Luteoxanthin, all-trans-
UNII-RXY7LCI9J0
RXY7LCI9J0
1912-50-1
7-Oxabicyclo(4.1.0)heptane, beta,beta-carotene-3,3'-diol deriv.
Beta-Carotene-3,3'-diol, 5,6:5',8'-diepoxy-5,5',6,8'-tetrahydro-
Beta,beta-Carotene-3,3'-diol, 5,6:5',8'-diepoxy-5,5',6,8'-tetrahydro-
CHEBI:35334
(6S,7aR)-2-((2E,4E,6E,8E,10E,12E,14E,16E)-17-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo(4.1.0)heptan-1-yl)-6,11,15-trimethylheptadeca-2,4,6,8,10,12,14,16-octaen-2-yl)-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol
(6S,7aR)-2-[(2E,4E,6E,8E,10E,12E,14E,16E)-17-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-6,11,15-trimethylheptadeca-2,4,6,8,10,12,14,16-octaen-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol
5,6:5',8'-Diepoxy-5,6,5',8'-tetrahydro-b,b-carotene-3,3'-diol
5,6:5',8'-Diepoxy-5,6,5',8'-tetrahydro-I2,I2-carotene-3,3'-diol
.BETA.,.BETA.-CAROTENE-3,3'-DIOL, 5,6:5',8'-DIEPOXY-5,5',6,8'-TETRAHYDRO-
.BETA.-CAROTENE-3,3'-DIOL, 5,6:5',8'-DIEPOXY-5,5',6,8'-TETRAHYDRO-
SCHEMBL980775
YNNRPBRNWWIQPQ-MAAFUUECSA-N
LMPR01070301
- 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]
No compound-protein relationship available.
SMILES: C1CCCC(O2)C12C=CC=CC=CC=CC=CC=CC=CC=CC(C3)OC(C=34)CCCC4
Level: 1
Mol. Weight: 600.88 g/mol
SMILES: C1COC(C=12)CCCC2
Level: 0
Mol. Weight: 600.88 g/mol
SMILES: C12C(O2)CCCC1
Level: 0
Mol. Weight: 600.88 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.82
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.92
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 2.64
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.61
- Plasma Protein Binding
- 90.38
- 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
- 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
- 3.83
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.54
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.54
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 8.55
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Toxic
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -11023.23
- Rat (Acute)
- 3.73
- Rat (Chronic Oral)
- 2.07
- Fathead Minnow
- 33.64
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Toxic
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 342.9
- Hydration Free Energy
- -2.95
- Log(D) at pH=7.4
- 6.51
- Log(P)
- 8.62
- Log S
- -6.88
- Log(Vapor Pressure)
- -10.04
- Melting Point
- 180.25
- pKa Acid
- 11.62
- pKa Basic
- 3.88
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Vitamin D(3) 25-hydroxylase | C4B644 | CPVDH_PSEAH | Pseudonocardia autotrophica | 3 | 0.9782 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.9359 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.8985 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8974 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.8944 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8827 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8738 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8721 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8715 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8712 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.8691 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.8572 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.8556 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8522 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8420 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.8411 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 3 | 0.8327 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.8291 |
| Retinol-binding protein 2 | P50120 | RET2_HUMAN | Homo sapiens | 3 | 0.8249 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.8181 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8085 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8044 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7993 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7978 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.7961 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 3 | 0.7926 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7843 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7800 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7699 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7606 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7600 |
| Beta-elicitin cryptogein | P15570 | ELIB_PHYCR | Phytophthora cryptogea | 3 | 0.7549 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7508 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.7491 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7437 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7376 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7336 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7311 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7303 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7288 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7255 |
| Cholesterol side-chain cleavage enzyme, mitochondrial | P05108 | CP11A_HUMAN | Homo sapiens | 3 | 0.7254 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 3 | 0.7244 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7240 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7229 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7206 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7188 |
| Peroxisome proliferator-activated receptor alpha | Q07869 | PPARA_HUMAN | Homo sapiens | 3 | 0.7153 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.7143 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7127 |
| Retinoic acid receptor gamma | P13631 | RARG_HUMAN | Homo sapiens | 3 | 0.7125 |
| Japanin | M1MR49 | M1MR49_RHIAP | Rhipicephalus appendiculatus | 3 | 0.7095 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7075 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7025 |
| Endoplasmin, putative | Q8I0V4 | Q8I0V4_PLAF7 | Plasmodium falciparum | 3 | 0.7019 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7006 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7005 |