Capsanthin

Details

• Internal ID: 7bd8599d-756f-4795-b7ff-ea080dd1c76f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Tetraterpenoids > Carotenoids > Xanthophylls
• IUPAC Name: (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
• InChI: InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-23-36-33(5)25-34(41)26-38(36,6)7)15-11-12-16-30(2)18-14-20-32(4)22-24-37(43)40(10)28-35(42)27-39(40,8)9/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t34-,35+,40+/m1/s1
• InChI Key: VYIRVAXUEZSDNC-RDJLEWNRSA-N
• Popularity: 846 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₆O₃
• Molecular Weight: 584.90 g/mol
• Exact Mass: 584.42294564 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 10.60
• Atomic LogP (AlogP): 9.81
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 11

Synonyms

• 465-42-9
• all-trans-capsanthin
• Capsanthin/capsorubin
• (3R,3'S,5'R)-3,3'-Dihydroxy-beta,kappa-caroten-6'-one
• CHEBI:3375
• DTXSID10905012
• 420NY1J57N
• beta,kappa-Caroten-6'one, 3,3'dihydroxy-
• (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
• (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-((4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-1-((1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
• RefChem:31613
• DTXCID401334125
• 207-364-1
• MFCD31726206
• (2E,4E,6E,8E,10E,12E,14E,16E,18E)-1-((1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl)-19-((R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
• 3,3'-Dihydroxy-beta,kappa-caroten-6'one
• all trans Capsanthin
• EINECS 207-364-1
• UNII-420NY1J57N
• Paprika Red
• HSDB 7977
• VYIRVAXUEZSDNC-RDJLEWNRSA-N
• CAPSANTHIN [MI]
• UPCMLD-DP025
• AC1NQY83
• SCHEMBL117691
• SPECTRUM1505276
• orb1984218
• CHEMBL1519371
• UPCMLD-DP025:001
• MSK2442
• Capsanthin, >=90.0% (HPLC)
• LMPR01070265
• AKOS040761459
• CCG-214238
• FC69781
• SDCCGMLS-0066894.P001
• NCGC00161603-01
• HY-125711
• CS-0093389
• NS00013435
• C08584
• D89295
• A827066
• Q425431
• SR-05000002758
• SR-05000002758-1
• 3,3'-DIHYDROXY-.BETA.,.KAPPA.-CAROTEN-6'ON
• I14-56396
• .BETA.,.KAPPA.-CAROTEN-6'ONE, 3,3'DIHYDROXY-
• (3R,3'S,5'R)-3,3'-DIHYDROXY-.BETA.,.KAPPA.-CAROTEN-6'-ONE
• (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
• (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethyl-1-cyclohexenyl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethyl-1-nonadeca-2,4,6,8,10,12,14,16,18-nonaenone
• (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethyl-cyclohexen-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethyl-cyclopentyl]-4,8,13,17-tetramethyl-nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
• (2E,4E,6E,8E,10E,12E,14E,16E,18E)-4,8,13,17-tetramethyl-19-[(4R)-2,6,6-trimethyl-4-oxidanyl-cyclohexen-1-yl]-1-[(1R,4S)-1,2,2-trimethyl-4-oxidanyl-cyclopentyl]nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
• 2,4,6,8,10,12,14,16,18-NONADECANONAEN-1-ONE, 19-(4-HYDROXY-2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-1-(4-HYDROXY-1,2,2-TRIMETHYLCYCLOPENTYL)-4,8,13,17-TETRAMETHYL-, (ALL-E)-
• 2,4,6,8,10,12,14,16,18-NONADECANONAEN-1-ONE, 19-(4-HYDROXY-2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-1-(5-HYDROXY-1,2,2-TRIMETHYLCYCLOPENTYL)-4,8,13,17-TETRAMETHYL-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9969	99.69%
Caco-2	-	0.7954	79.54%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7774	77.74%
OATP2B1 inhibitior	+	0.5720	57.20%
OATP1B1 inhibitior	+	0.9356	93.56%
OATP1B3 inhibitior	+	0.9527	95.27%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9969	99.69%
P-glycoprotein inhibitior	+	0.7975	79.75%
P-glycoprotein substrate	-	0.6126	61.26%
CYP3A4 substrate	+	0.6677	66.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8511	85.11%
CYP3A4 inhibition	-	0.8532	85.32%
CYP2C9 inhibition	-	0.8816	88.16%
CYP2C19 inhibition	-	0.8846	88.46%
CYP2D6 inhibition	-	0.9544	95.44%
CYP1A2 inhibition	-	0.9285	92.85%
CYP2C8 inhibition	-	0.7056	70.56%
CYP inhibitory promiscuity	-	0.8784	87.84%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7957	79.57%
Carcinogenicity (trinary)	Non-required	0.5505	55.05%
Eye corrosion	-	0.9846	98.46%
Eye irritation	-	0.9110	91.10%
Skin irritation	+	0.5940	59.40%
Skin corrosion	-	0.9689	96.89%
Ames mutagenesis	-	0.5091	50.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.7455	74.55%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6781	67.81%
skin sensitisation	+	0.7601	76.01%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.7347	73.47%
Acute Oral Toxicity (c)	III	0.4781	47.81%
Estrogen receptor binding	+	0.8330	83.30%
Androgen receptor binding	+	0.7636	76.36%
Thyroid receptor binding	+	0.7252	72.52%
Glucocorticoid receptor binding	+	0.8319	83.19%
Aromatase binding	-	0.5248	52.48%
PPAR gamma	+	0.7137	71.37%
Honey bee toxicity	-	0.8265	82.65%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9855	98.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.82%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.86%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.81%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.24%	89.00%
CHEMBL1870	P28702	Retinoid X receptor beta	84.75%	95.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.21%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.75%	86.33%
CHEMBL2004	P48443	Retinoid X receptor gamma	81.64%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.52%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.73%	96.00%

Plants that contains it

• Capsicum annuum
• Lilium lancifolium

Cross-Links

• PubChem: 5281228
• NPASS: NPC183736
• ChEMBL: CHEMBL1519371
• LOTUS: LTS0213437
• wikiData: Q425431