(2S)-2-Hydroxybutanedioic acid

Details

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Internal ID 0a31c581-9687-4c61-9939-c17b191f5e47
Taxonomy Organic acids and derivatives > Hydroxy acids and derivatives > Beta hydroxy acids and derivatives
IUPAC Name (2S)-2-hydroxybutanedioic acid
SMILES (Canonical) C(C(C(=O)O)O)C(=O)O
SMILES (Isomeric) C([C@@H](C(=O)O)O)C(=O)O
InChI InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
InChI Key BJEPYKJPYRNKOW-REOHCLBHSA-N
Popularity 1,573 references in papers

Physical and Chemical Properties

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Molecular Formula C4H6O5
Molecular Weight 134.09 g/mol
Exact Mass 134.02152329 g/mol
Topological Polar Surface Area (TPSA) 94.80 Ų
XlogP -1.30
Atomic LogP (AlogP) -1.09
H-Bond Acceptor 3
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

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L-Malic acid
L-(-)-Malic acid
(S)-2-hydroxysuccinic acid
(2S)-2-Hydroxybutanedioic acid
(S)-Malic acid
L(-)-Malic acid
Apple acid
(-)-Malic acid
L-Apple acid
(-)-Hydroxysuccinic acid
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of (2S)-2-Hydroxybutanedioic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.5822 58.22%
Caco-2 - 0.9584 95.84%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability + 0.6143 61.43%
Subcellular localzation Mitochondria 0.6921 69.21%
OATP2B1 inhibitior - 0.8555 85.55%
OATP1B1 inhibitior + 0.9522 95.22%
OATP1B3 inhibitior + 0.9499 94.99%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 1.0000 100.00%
BSEP inhibitior - 0.9789 97.89%
P-glycoprotein inhibitior - 0.9837 98.37%
P-glycoprotein substrate - 0.9914 99.14%
CYP3A4 substrate - 0.7875 78.75%
CYP2C9 substrate + 0.5992 59.92%
CYP2D6 substrate - 0.8355 83.55%
CYP3A4 inhibition - 0.9066 90.66%
CYP2C9 inhibition - 0.9691 96.91%
CYP2C19 inhibition - 0.9716 97.16%
CYP2D6 inhibition - 0.9587 95.87%
CYP1A2 inhibition - 0.9521 95.21%
CYP2C8 inhibition - 0.9956 99.56%
CYP inhibitory promiscuity - 0.9934 99.34%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.7830 78.30%
Carcinogenicity (trinary) Non-required 0.7593 75.93%
Eye corrosion - 0.7563 75.63%
Eye irritation + 0.9629 96.29%
Skin irritation + 0.6209 62.09%
Skin corrosion - 0.8853 88.53%
Ames mutagenesis - 0.7500 75.00%
Human Ether-a-go-go-Related Gene inhibition - 0.8293 82.93%
Micronuclear - 0.5700 57.00%
Hepatotoxicity + 0.6000 60.00%
skin sensitisation - 0.9393 93.93%
Respiratory toxicity - 0.8667 86.67%
Reproductive toxicity - 0.8333 83.33%
Mitochondrial toxicity - 0.9000 90.00%
Nephrotoxicity - 0.5751 57.51%
Acute Oral Toxicity (c) III 0.8028 80.28%
Estrogen receptor binding - 0.9037 90.37%
Androgen receptor binding - 0.8133 81.33%
Thyroid receptor binding - 0.8670 86.70%
Glucocorticoid receptor binding - 0.7970 79.70%
Aromatase binding - 0.8803 88.03%
PPAR gamma - 0.7575 75.75%
Honey bee toxicity - 0.9330 93.30%
Biodegradation + 0.9500 95.00%
Crustacea aquatic toxicity - 0.9100 91.00%
Fish aquatic toxicity - 0.7957 79.57%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 88.84% 96.09%
CHEMBL2581 P07339 Cathepsin D 88.23% 98.95%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 83.45% 96.95%
CHEMBL221 P23219 Cyclooxygenase-1 83.44% 90.17%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.00% 99.17%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 81.27% 85.14%
CHEMBL1907591 P30926 Neuronal acetylcholine receptor; alpha4/beta4 81.00% 100.00%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 80.12% 97.21%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Aconitum seravschanicum
Acorus calamus
Adansonia grandidieri
Alkekengi officinarum
Aloe
Aloe africana
Aloe arborescens
Aloe ferox
Aloe spicata
Aloe vera
Alstonia muelleriana
Angelica acutiloba
Angelica gigas
Angelica sinensis
Aphyllocladus denticulatus
Arabidopsis thaliana
Arbutus unedo
Bassia muricata
Bupleurum chinense
Bupleurum falcatum
Bupleurum scorzonerifolium
Capsicum annuum
Chaenomeles sinensis
Chelidonium majus
Cichorium intybus
Cichorium pumilum
Combretum indicum
Coreopsis nodosa
Cornus officinalis
Dacrydium cupressinum
Dendriopoterium menendezii
Dianthera secunda
Dodonaea viscosa
Dysoxylum cumingianum
Eleusine coracana
Enceliopsis argophylla
Euphorbia pereskiifolia
Flacourtia inermis
Flacourtia jangomas
Galatella sedifolia subsp. sedifolia
Glaucium flavum
Glycine tomentella
Hippophae rhamnoides
Homalomena occulta
Isatis tinctoria
Lavandula angustifolia subsp. pyrenaica
Lepidium meyenii
Melia azedarach
Miliusa velutina
Neobalanocarpus heimii
Nicotiana undulata
Onobrychis arenaria
Opuntia stricta
Paeonia suffruticosa
Parasenecio hastatus
Passiflora incarnata
Persicaria tinctoria
Phyllanthus emblica
Plantago major
Prunus avium
Prunus mume
Psychotria stachyoides
Punica granatum
Rehmannia glutinosa
Reynoutria japonica
Rheum rhabarbarum
Rubia argyi
Schisandra chinensis
Schisandra sphenanthera
Scutellaria baicalensis
Senecio paludaffinis
Senecio subdentatus
Seriphidium cinum
Tamarindus indica
Taraxacum coreanum
Taraxacum mongolicum
Taraxacum officinale
Taraxacum platycarpum
Taraxacum sinicum
Teucrium yemense
Trichotosia mollis
Trigonella grandiflora
Tripolium pannonicum
Tussilago farfara
Uvaria calamistrata
Vaccinium macrocarpon
Viburnum opulus
Wurfbainia neoaurantiaca
Ziziphus jujuba

Cross-Links

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PubChem 222656
NPASS NPC3357
LOTUS LTS0128885
wikiData Q27104150