Ectoine

Details

• Internal ID: 0491886d-c49d-4f74-a85c-42728cb9b956
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acids > L-alpha-amino acids
• IUPAC Name: (6S)-2-methyl-1,4,5,6-tetrahydropyrimidine-6-carboxylic acid
• SMILES (Canonical): CC1=NCCC(N1)C(=O)O
• SMILES (Isomeric): CC1=NCC[C@H](N1)C(=O)O
• InChI: InChI=1S/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1
• InChI Key: WQXNXVUDBPYKBA-YFKPBYRVSA-N
• Popularity: 1,012 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₀N₂O₂
• Molecular Weight: 142.16 g/mol
• Exact Mass: 142.074227566 g/mol
• Topological Polar Surface Area (TPSA): 61.70 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.15
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 96702-03-3
• ectoin
• 7GXZ3858RY
• (4S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
• (6S)-2-methyl-1,4,5,6-tetrahydropyrimidine-6-carboxylic acid
• CHEBI:27592
• DTXSID50869280
• NSC-614616
• 1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acid
• (4S)-3,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acid
• (4S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylate
• (6S)-2-methyl-1,4,5,6-tetrahydropyrimidin-3-ium-6-carboxylate
• 4-Pyrimidinecarboxylic acid, 1,4,5,6-tetrahydro-2-methyl-, (+)-
• RefChem:590567
• DTXCID001765744
• 2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
• NSC614616
• L-Ectoine
• (S)-2-Methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
• (S)-2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
• MFCD03419286
• 4-Pyrimidinecarboxylicacid, 3,4,5,6-tetrahydro-2-methyl-, (4S)-
• (S)-2-Methyl- 1,4,5,6-tetrahydropyrimidine-4-carboxylic acid
• (+)-1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid
• UNII-7GXZ3858RY
• SMR000127407
• (S)-1,4,5,6-Tetrahydro-2-methyl-4-pyrimidincarbonsure
• Ectoine?
• 4CS
• Ectoine (Standard)
• Ectoine, osmoprotectant
• ECTOINE [MI]
• ECTOINE [WHO-DD]
• SCHEMBL93532
• US9138393, Ectoine
• US9144538, Ectoine
• MLS001332487
• MLS001332488
• SCHEMBL977252
• orb1303265
• CHEMBL1230264
• BDBM181140
• Ectoine, >=95.0% (HPLC)
• EX-A1678
• 4-Pyrimidinecarboxylic acid, 1,4,5,6-tetrahydro-2-methyl-, (4S)-
• MSK160506
• s5591
• AKOS006348056
• AKOS027427031
• CCG-266161
• DS-3343
• EBC-616375
• FE44798
• HY-107784R
• NSC 614616
• AC-33942
• DA-63111
• SY223897
• HY-107784
• CS-0030647
• E1372
• C06231
• I11596
• Ectoine, primary pharmaceutical reference standard
• F541626
• Q414414
• (4S)-2-Methyl-1,4,5,6-tetrahydro-4-pyrimidinecarboxylic acid
• (4s)-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
• (S)-1,4,5,6-tetrahydro-2-methyl-4-pyrimi-dinecarboxylic acid
• (s)-1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid
• (S)-2-Methyl-3,4,5,6-tetrahydropyrimidine-4 carboxylic acid
• Ectoine (2-Methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9516	95.16%
Caco-2	-	0.7543	75.43%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5197	51.97%
OATP2B1 inhibitior	-	0.8283	82.83%
OATP1B1 inhibitior	+	0.9640	96.40%
OATP1B3 inhibitior	+	0.9475	94.75%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9645	96.45%
P-glycoprotein inhibitior	-	0.9898	98.98%
P-glycoprotein substrate	-	0.9099	90.99%
CYP3A4 substrate	-	0.5993	59.93%
CYP2C9 substrate	-	0.5790	57.90%
CYP2D6 substrate	-	0.8752	87.52%
CYP3A4 inhibition	-	0.9816	98.16%
CYP2C9 inhibition	-	0.9523	95.23%
CYP2C19 inhibition	-	0.9614	96.14%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.8913	89.13%
CYP2C8 inhibition	-	0.9824	98.24%
CYP inhibitory promiscuity	-	1.0000	100.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.7059	70.59%
Eye corrosion	-	0.9593	95.93%
Eye irritation	-	0.4886	48.86%
Skin irritation	-	0.6952	69.52%
Skin corrosion	-	0.7815	78.15%
Ames mutagenesis	-	0.8244	82.44%
Human Ether-a-go-go-Related Gene inhibition	-	0.7784	77.84%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.6860	68.60%
skin sensitisation	-	0.8443	84.43%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6233	62.33%
Acute Oral Toxicity (c)	III	0.5738	57.38%
Estrogen receptor binding	-	0.9048	90.48%
Androgen receptor binding	-	0.7986	79.86%
Thyroid receptor binding	-	0.8863	88.63%
Glucocorticoid receptor binding	-	0.9171	91.71%
Aromatase binding	-	0.8284	82.84%
PPAR gamma	-	0.7626	76.26%
Honey bee toxicity	-	0.9868	98.68%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	-	0.9402	94.02%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.79%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.18%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.11%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.82%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.56%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.56%	97.09%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	80.89%	97.64%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 126041
• LOTUS: LTS0275429
• wikiData: Q414414