Fucoxanthin - Compound Card

Fucoxanthin

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Fucoxanthin

Structure
Zoomed Structure
  • Family: Chromista - Sphacelariaceae
  • Kingdom: Chromista
  • Class: Terpenoid
    • Subclass: Apo-Fucoxanthinoid
Canonical Smiles C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)C[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)OC(=O)C)\C
InChI InChI=1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23?,34-,35-,40+,41+,42-/m0/s1
InChIKey SJWWTRQNNRNTPU-ABBNZJFMSA-N
Formula C42H58O6
HBA 6
HBD 2
MW 658.92
Rotatable Bonds 11
TPSA 96.36
LogP 8.69
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 48
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 658.42
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Cladostephus spongiosus f. verticillatus Sphacelariaceae Chromista 74470

Showing of synonyms

  • El Hattab M, Culioli G, et al. (2008). Apo-fucoxanthinoids and loliolide from the brown alga Cladostephus spongiosus f. verticillatus (Heterokonta, Sphacelariales). Biochemical Systematics and Ecology,2008,36(5-6),447-451. [View]
CPRiL: 59794
Structure

SMILES: C1CCCCC1=C=CC=CC=CC=CC=CC=CC=CC=CC(=O)CC23C(O3)CCCC2

Level: 1

Mol. Weight: 658.92 g/mol

Structure

SMILES: C=C=C1CCCCC1

Level: 0

Mol. Weight: 658.92 g/mol

Structure

SMILES: C12C(O2)CCCC1

Level: 0

Mol. Weight: 658.92 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.74
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
23.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.55
Plasma Protein Binding
98.85
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
4.85
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.94
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.3
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
8.2
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-48743.64
Rat (Acute)
3.93
Rat (Chronic Oral)
2.08
Fathead Minnow
87.52
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
2115.34
Hydration Free Energy
-2.92
Log(D) at pH=7.4
6.07
Log(P)
7.68
Log S
-6.9
Log(Vapor Pressure)
-100.69
Melting Point
174.76
pKa Acid
12.23
pKa Basic
3.27
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 0.9501
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.9501
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9027
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9027
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8897
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8897
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8887
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8887
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8513
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8513
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8381
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8381
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8233
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8233
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8208
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8208
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8177
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8177
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8066
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8066
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8033
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8033
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8007
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8007
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8006
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8006
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7981
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7981
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7917
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7917
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7906
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7906
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7888
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7888
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7861
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7861
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7802
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7802
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7722
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7722
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7718
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7718
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7685
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7685
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7609
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7609
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7587
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7587
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7576
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7576
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7562
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7562
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7561
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7561
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7553
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7553
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7541
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7541
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7482
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7482
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7476
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7476
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7467
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7467
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7454
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7454
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7446
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7446
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7434
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7434
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7429
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7429
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7426
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7426
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7425
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7425
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7410
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7410
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7389
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7389
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7371
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7371
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7368
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7368
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7353
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7353
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7329
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7329
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7324
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7324
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7309
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7309
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7301
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7301
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7256
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7256
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7240
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7240
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7186
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7186
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7174
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7174
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7168
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7168
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7163
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7163
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7162
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7162
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7152
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7152
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 4 0.7131
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 4 0.7131
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7127
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7127
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7123
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7123
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7121
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7121
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7113
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7113
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7099
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7099
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7097
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7097
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7056
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7056
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7032
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7032
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7031
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7031
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7027
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7027
Bile acid receptor Q62735 NR1H4_RAT Rattus norvegicus 4 0.7008
Bile acid receptor Q62735 NR1H4_RAT Rattus norvegicus 4 0.7008

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