Rosmarinic acid

Details

• Internal ID: 3406af2c-ffcf-4b7c-84dc-cf5b7bec9219
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
• InChI: InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+/t16-/m1/s1
• InChI Key: DOUMFZQKYFQNTF-WUTVXBCWSA-N
• Popularity: 3,695 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₈
• Molecular Weight: 360.30 g/mol
• Exact Mass: 360.08451746 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.76
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• 20283-92-5
• Rosemary acid
• Labiatenic acid
• Rosmarinicacid
• Labiatic acid
• (R)-rosmarinic acid
• trans-Rosmarinic acid
• Rosemaric acid
• Rosmarinic acid racemate
• Rosmarinate
• Rosmarinic-acid
• UNII-MQE6XG29YI
• MQE6XG29YI
• CCRIS 9361
• RM 21A
• 537-15-5
• ORISTRACT ROA
• HSDB 7688
• NPLC 0542
• (R,E)-3-(3,4-dihydroxyphenyl)-2-((3-(3,4-dihydroxyphenyl)acryloyl)oxy)propanoic acid
• (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoic acid
• CHEMBL324842
• RM-21A
• CHEBI:50371
• NPLC-0542
• DTXSID20896987
• (R)-O-(3,4-Dihydroxycinnamoyl)-3-(3,4- dihydroxyphenyl)lactic acid
• Benzenepropanoic acid, alpha-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy-
• C18H16O8
• (R)-O-(3,4-Dihydroxycinnamoyl)-3-(3,4-dihydroxyphenyl)lactic acid
• 3,4-Dihydroxycinnamic acid 2-ester with 3-(3,4-dihydroxyphenyl)lactic acid
• R-(+)-2-(3,4-Dihydroxycinnamoyloxy)-3-(3,4-dihydroxyphenyl)propionic acid
• (2R)-3-(3,4-dihydroxyphenyl)-2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]propanoic acid
• (2r)-3-(3,4-Dihydroxyphenyl)-2-{[(2e)-3-(3,4-Dihydroxyphenyl)prop-2-Enoyl]oxy}propanoic Acid
• CINNAMIC ACID, 3,4-DIHYDROXY-, 2-ESTER with 3-(3,4-DIHYDROXYPHENYL)LACTIC ACID
• ROSMARINIC ACID (USP-RS)
• ROSMARINIC ACID [USP-RS]
• (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-propanoic acid
• alpha-(((3,4-Dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxybenzenepropanoic acid
• Benzenepropanoic acid, alpha-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy-, (R-(E))-
• 3,4-Dihydroxycinnamic acid (R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl ester
• Rosmarimic acid
• BENZENEPROPANOIC ACID, .ALPHA.-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-3,4-DIHYDROXY-, (.ALPHA.R)-
• Benzenepropanoic acid, .alpha.-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy-, (R-(E))-
• Benzenepropanoic acid, .alpha.-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-, (.alpha.R)-
• Benzenepropanoic acid, .alpha.-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-, [R-(E)]-
• MFCD00017740
• Rosmarinic acid, 2
• Rosmarinic acid, 96%
• bmse000648
• D05PTT
• ROSMARINIC ACID [MI]
• MLS000697677
• ROSMARINIC ACID [HSDB]
• ROSMARINIC ACID [INCI]
• MEGxp0_000163
• SCHEMBL1650675
• SCHEMBL2028694
• ACon1_001068
• CHEBI:92370
• cid_5281792
• 3-(3,4-dihydroxyphenyl)-2-((2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy)propanoic acid
• DOUMFZQKYFQNTF-WUTVXBCWSA-N
• DTXCID801326415
• HMS2227A13
• HMS3266D13
• HMS3411K16
• HMS3649C22
• HMS3675K16
• HMS3885I15
• HY-N0529
• BDBM50133496
• s3612
• ZB1872
• AKOS015892734
• CCG-207919
• CCG-208268
• NCGC00169708-01
• AC-33965
• AS-35341
• Benzenepropanoic acid,a-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-,(aR)-
• SMR000445579
• LS-175479
• C01850
• EN300-364852
• ROSMARINIC ACID (CONSTITUENT OF ROSEMARY)
• A814378
• SR-01000946599
• Q-100246
• SR-01000946599-1
• (2R)-O-caffeoyl-3-(3,4-dihydroxyphenyl)lactic acid
• Q50380051
• F0001-0715
• ROSMARINIC ACID (CONSTITUENT OF HOLY BASIL LEAF)
• ROSMARINIC ACID (CONSTITUENT OF ROSEMARY) [DSC]
• 93B6A3BF-927D-4C59-8A49-29BDBC87C194
• Rosmarinic acid, primary pharmaceutical reference standard
• ROSMARINIC ACID (CONSTITUENT OF HOLY BASIL LEAF) [DSC]
• Rosmarinic acid, European Pharmacopoeia (EP) Reference Standard
• Rosmarinic acid, >=98% (HPLC), from Rosemarinus officinalis L.
• Rosmarinic acid, United States Pharmacopeia (USP) Reference Standard
• (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoicacid
• (R)-2-[3-(3,4-Dihydroxyphenyl)acryloyloxy]-3-(3,4-dihydroxyphenyl)propionic acid
• (R,E)-3-(3,4-dihydroxyphenyl)-2-((3-(3,4-dihydroxyphenyl)acryloyl)oxy)propanoicacid
• (R,E)-3-(3,4-dihydroxyphenyl)-2-(3-(3,4-dihydroxyphenyl)acryloyloxy)propanoic acid
• 3-(3,4-DIHYDROXYPHENYL)ACRYLIC ACID-1-CARBOXY-2-(3,4-DIHYDROXYPHENYL)ETHYL ESTER
• alpha-(((3,4-Dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy-benzenepropanoic acid
• (2R)-3-(3,4-DIHYDROXYPHENYL)-2-{[3-(3,4-DIHYDROXYPHENYL)PROP-2-ENOYL]OXY}PROPANOIC ACID
• (alpha R)-alpha-[[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3,4-dihydroxybenzenepropanoic acid
• [R-(+)]-?-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxybenzenepropanoic acid
• 162281-84-7
• BENZENEPROPANOIC ACID, .ALPHA.-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4-DIHYDROXY-, (.ALPHA.R)-
• BENZENEPROPANOIC ACID, alpha-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4-DIHYDROXY-, (alphaR)-
• BENZENEPROPANOIC ACID, alpha-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-3,4-DIHYDROXY-, (alphaR)-
• Propanoic acid, 3- (3, 4- dihydroxyphenyl)- 2- [3- (3, 4- dihydroxyphenyl)- 1- oxo- 2- propenyloxy]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8756	87.56%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8306	83.06%
OATP2B1 inhibitior	-	0.5749	57.49%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	+	0.5200	52.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6882	68.82%
P-glycoprotein inhibitior	-	0.8529	85.29%
P-glycoprotein substrate	-	0.9340	93.40%
CYP3A4 substrate	-	0.5802	58.02%
CYP2C9 substrate	-	0.5979	59.79%
CYP2D6 substrate	-	0.8612	86.12%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8754	87.54%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.6279	62.79%
CYP2C8 inhibition	+	0.5112	51.12%
CYP inhibitory promiscuity	-	0.8300	83.00%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8141	81.41%
Carcinogenicity (trinary)	Non-required	0.6152	61.52%
Eye corrosion	-	0.9895	98.95%
Eye irritation	+	0.5264	52.64%
Skin irritation	-	0.7211	72.11%
Skin corrosion	-	0.9416	94.16%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4806	48.06%
Micronuclear	+	0.7159	71.59%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.5655	56.55%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8974	89.74%
Acute Oral Toxicity (c)	III	0.7720	77.20%
Estrogen receptor binding	+	0.8228	82.28%
Androgen receptor binding	+	0.8585	85.85%
Thyroid receptor binding	+	0.5265	52.65%
Glucocorticoid receptor binding	+	0.6399	63.99%
Aromatase binding	-	0.5927	59.27%
PPAR gamma	+	0.5798	57.98%
Honey bee toxicity	-	0.7466	74.66%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9952	99.52%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1900	P15121	Aldose reductase	3910 nM	IC50	PMID: 20071057
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	3548.1 nM	Potency	via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	22387.2 nM	Potency	via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	223.9 nM; 223.9 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	631 nM; 631 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25.1 nM	Potency	via Super-PRED
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	2025.72 nM	IC50	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	14125.4 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	2511.9 nM	Potency	via CMAUP
CHEMBL332	P03956	Matrix metalloproteinase-1	5600 nM	IC50	PMID: 23353736
CHEMBL1293224	P10636	Microtubule-associated protein tau	12589.3 nM; 14125.4 nM; 17782.8 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL4977	P05412	Proto-oncogene c-JUN	16200 nM	IC50	PMID: 24491635
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	1000 nM; 1000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	25118.9 nM; 44668.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3194	P02766	Transthyretin	8600 nM	EC50	PMID: 25314129
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	1300 nM; 3600 nM; 17000 nM; 36000 nM; 63000 nM; 74000 nM	IC50; IC50; IC50; IC50; IC50; IC50	PMID: 17315853; PMID: 17315853; PMID: 17315853; PMID: 17315853; PMID: 17315853; PMID: 17315853
CHEMBL258	P06239	Tyrosine-protein kinase LCK	24000 nM; 55000 nM	IC50; IC50	PMID: 14505648; PMID: 19427202
CHEMBL267	P12931	Tyrosine-protein kinase SRC	26000 nM	IC50	PMID: 19427202
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	223.9 nM; 223.9 nM; 891.3 nM	Potency; Potency; Potency	via CMAUP; via Super-PRED; via Super-PRED
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	25118.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.69%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.94%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.33%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.20%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.01%	99.17%
CHEMBL3194	P02766	Transthyretin	92.66%	90.71%
CHEMBL4040	P28482	MAP kinase ERK2	92.41%	83.82%
CHEMBL2581	P07339	Cathepsin D	91.23%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.96%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.95%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	88.66%	90.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.08%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.53%	95.50%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.43%	91.71%
CHEMBL1255126	O15151	Protein Mdm4	81.75%	90.20%

Plants that contains it

• Aconitum leucostomum
• Agastache rugosa
• Aiouea montana
• Anchusa officinalis
• Anchusa strigosa
• Anthoceros punctatus
• Anthurium versicolor
• Apeiba tibourbou
• Aquilegia ecalcarata
• Arnebia euchroma
• Arnebia guttata
• Artemisia annua
• Artemisia carvifolia
• Artemisia szowitziana
• Astrantia major
• Blechnum gibbum
• Blumea axillaris
• Ceanothus velutinus
• Centella asiatica
• Chlorophytum borivilianum
• Clinopodium chinense
• Clinopodium laxiflorum
• Clinopodium umbrosum
• Condea verticillata
• Coriandrum sativum
• Crataegus laevigata
• Dipterocarpus dyeri
• Ehretia microphylla
• Ehretia philippinensis
• Foeniculum vulgare
• Fragaria vesca
• Gamblea innovans
• Garcinia scortechinii
• Gardenia tubifera
• Glechoma grandis
• Glechoma hederacea
• Glechoma longituba
• Hamelia patens
• Hedeoma drummondii
• Hedera helix
• Helicteres angustifolia
• Heliotropium arborescens
• Heliotropium sarmentosum
• Hyptis capitata
• Hyssopus officinalis
• Ipomoea cairica
• Isodon coetsa
• Isodon japonicus
• Isodon lophanthoides
• Isodon oresbius
• Isodon rubescens
• Isodon sculponeatus
• Kopsia grandifolia
• Lasianthus fordii
• Lavandula angustifolia subsp. angustifolia
• Lavandula intermedia
• Ledebouria socialis
• Lithospermum erythrorhizon
• Lycopus asper
• Lycopus europaeus
• Lycopus lucidus
• Melissa officinalis
• Mentha × piperita
• Mentha arvensis
• Mentha canadensis
• Mentha spicata
• Momordica charantia
• Mosla dianthera
• Myristica fragrans
• Nepeta italica subsp. cadmea
• Ocimum americanum
• Ocimum basilicum
• Ocimum tenuiflorum
• Origanum vulgare
• Orthosiphon aristatus var. aristatus
• Perilla frutescens
• Persea barbujana
• Plantago lagopus
• Plectranthus amboinicus
• Plectranthus ovatus
• Plectranthus scutellarioides
• Prunella vulgaris
• Rhododendron dauricum
• Rosmarinus officinalis
• Rubia argyi
• Salvia cavaleriei
• Salvia chinensis
• Salvia deserta
• Salvia flava
• Salvia fruticosa
• Salvia miltiorrhiza
• Salvia officinalis
• Salvia prionitis
• Salvia przewalskii
• Salvia trijuga
• Salvia yunnanensis
• Sanicula europaea
• Sarcandra glabra
• Smilax china
• Smilax glabra
• Symphytum officinale
• Teucrium scorodonia
• Thalassia hemprichii
• Thymus bashkiriensis
• Thymus guberlinensis
• Thymus quinquecostatus
• Thymus vulgaris
• Trigonotis peduncularis
• Triumfetta rhomboidea
• Vaccinium arctostaphylos
• Zataria multiflora

Cross-Links

• PubChem: 5281792
• NPASS: NPC61
• ChEMBL: CHEMBL324842
• LOTUS: LTS0207820
• wikiData: Q50380051