Shikimic acid

Details

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Internal ID 2b24c866-f572-4f46-9529-1bcb33762d45
Taxonomy Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Shikimic acids and derivatves
IUPAC Name (3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
SMILES (Canonical) C1C(C(C(C=C1C(=O)O)O)O)O
SMILES (Isomeric) C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)O
InChI InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1
InChI Key JXOHGGNKMLTUBP-HSUXUTPPSA-N
Popularity 1,825 references in papers

Physical and Chemical Properties

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Molecular Formula C7H10O5
Molecular Weight 174.15 g/mol
Exact Mass 174.05282342 g/mol
Topological Polar Surface Area (TPSA) 98.00 Ų
XlogP -1.70
Atomic LogP (AlogP) -1.52
H-Bond Acceptor 4
H-Bond Donor 4
Rotatable Bonds 1

Synonyms

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138-59-0
shikimate
L-Shikimic acid
(-)-Shikimic acid
(3R,4S,5R)-3,4,5-TRIHYDROXYCYCLOHEX-1-ENE-1-CARBOXYLIC ACID
(3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid
(3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
CCRIS 7681
1-cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)-
HSDB 3537
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Shikimic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7866 78.66%
Caco-2 - 0.9343 93.43%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability + 0.6429 64.29%
Subcellular localzation Mitochondria 0.7120 71.20%
OATP2B1 inhibitior - 0.8550 85.50%
OATP1B1 inhibitior + 0.9507 95.07%
OATP1B3 inhibitior + 0.9571 95.71%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9588 95.88%
BSEP inhibitior - 0.9860 98.60%
P-glycoprotein inhibitior - 0.9837 98.37%
P-glycoprotein substrate - 0.9760 97.60%
CYP3A4 substrate - 0.7137 71.37%
CYP2C9 substrate - 0.7723 77.23%
CYP2D6 substrate - 0.8802 88.02%
CYP3A4 inhibition - 0.9563 95.63%
CYP2C9 inhibition - 0.9372 93.72%
CYP2C19 inhibition - 0.9487 94.87%
CYP2D6 inhibition - 0.9366 93.66%
CYP1A2 inhibition - 0.9499 94.99%
CYP2C8 inhibition - 0.9810 98.10%
CYP inhibitory promiscuity - 0.9662 96.62%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9100 91.00%
Carcinogenicity (trinary) Non-required 0.6723 67.23%
Eye corrosion - 0.9714 97.14%
Eye irritation + 0.7389 73.89%
Skin irritation + 0.5051 50.51%
Skin corrosion - 0.9010 90.10%
Ames mutagenesis - 0.9300 93.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7895 78.95%
Micronuclear + 0.5659 56.59%
Hepatotoxicity + 0.5375 53.75%
skin sensitisation + 0.4766 47.66%
Respiratory toxicity - 0.5556 55.56%
Reproductive toxicity + 0.5889 58.89%
Mitochondrial toxicity - 0.6125 61.25%
Nephrotoxicity + 0.4628 46.28%
Acute Oral Toxicity (c) IV 0.4690 46.90%
Estrogen receptor binding - 0.8876 88.76%
Androgen receptor binding - 0.7785 77.85%
Thyroid receptor binding - 0.8108 81.08%
Glucocorticoid receptor binding - 0.8006 80.06%
Aromatase binding - 0.8835 88.35%
PPAR gamma - 0.8418 84.18%
Honey bee toxicity - 0.9141 91.41%
Biodegradation + 0.6000 60.00%
Crustacea aquatic toxicity - 0.7900 79.00%
Fish aquatic toxicity + 0.7319 73.19%

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 91.81% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 84.91% 91.11%
CHEMBL4040 P28482 MAP kinase ERK2 84.32% 83.82%
CHEMBL2581 P07339 Cathepsin D 82.72% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 81.98% 95.56%
CHEMBL1811 P34995 Prostanoid EP1 receptor 81.22% 95.71%

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.
Acacia simplicifolia
Acicarpha tribuloides
Aconitum palmatum
Aconitum rotundifolium
Acorus calamus
Albizia julibrissin
Alcea rosea
Alpinia roxburghii
Anacardium occidentale
Anchusa officinalis
Aniba rosaeodora
Annona muricata
Arabidopsis thaliana
Ariocarpus fissuratus
Balanops australiana
Bidens tripartita
Blasia pusilla
Boehmeria dura
Bowdichia virgilioides
Breonia chinensis
Callitris columellaris
Calophyllum brasiliense
Campylotropis hirtella
Carpesium faberi
Caryopteris mongholica
Castanopsis fissa
Centaurea zuccariniana
Ceropegia dichotoma
Chaenomeles sinensis
Cheirolophus arbutifolius
Cichorium intybus
Cichorium pumilum
Cirsium carolinianum
Cistus creticus
Cleistopholis patens
Codonopsis cordifolioidea
Corydalis sewerzowi
Corymbia citriodora
Cousinia canescens
Crinum moorei
Crotalaria candicans
Culcitium albifolium
Dahlstedtia pentaphylla
Dalbergia rubiginosa
Daucus carota
Davallia perdurans
Dendrobium fuscescens
Dendrobium loddigesii
Dicranopteris linearis
Dioscorea bulbifera
Dipentodon sinicus
Distephanus angulifolius
Erucastrum gallicum
Eucalyptus apodophylla
Euonymus tingens
Euphorbia cornigera
Euphorbia kansui
Excoecaria cochinchinensis
Firmiana simplex
Flemingia prostrata
Gardenia jasminoides
Genista sessilifolia
Ginkgo biloba
Glycosmis macrophylla
Gomphostemma parviflorum
Gonzalezia decurrens
Gypsophila perfoliata
Hasteola robusta
Hedyosmum bonplandianum
Hippobroma longiflora
Hirtellina fruticosa
Hydrangea chinensis
Hylocomium splendens
Hypericum beanii
Hypericum japonicum
Hypericum laricifolium
Hypericum monogynum
Hypericum oblongifolium
Hypericum perforatum
Hypericum polyanthemum
Illicium majus
Illicium simonsii
Illicium verum
Juniperus drupacea
Kielmeyera pumila
Kokoona reflexa
Leucopogon parviflorus
Liquidambar styraciflua
Lophostemon confertus
Loropetalum chinense
Lotus corniculatus subsp. corniculatus
Maesa ramentacea
Magnolia arcabucoana
Magnolia denudata
Mappia nimmoniana
Mentha × gentilis
Mesembryanthemum tortuosum
Millettia laurentii
Monodora tenuifolia
Nauclea parva
Ocimum tenuiflorum
Ononis spinosa
Onoseris alata
Orbivestus karaguensis
Panax ginseng
Panax stipuleanatus
Pentaclethra macrophylla
Pericome caudata
Periploca sepium
Pinalia japonica
Pinus pinaster
Pinus ponderosa
Pinus strobus
Pinus sylvestris
Piper acutifolium
Piper lanceifolium
Piptostigma fugax
Plectranthus hereroensis
Pluchea odorata
Pogostemon cablin
Populus lasiocarpa
Populus tremula
Prunus domestica
Psilotum nudum
Pteridium aquilinum
Pterocaulon virgatum
Rhodiola semenovii
Rubus idaeus
Salacia lehmbachii
Salvia sessei
Salvia yosgadensis
Satureja atropatana
Selaginella pulvinata
Selaginella tamariscina
Sequoiadendron giganteum
Sideritis brevibracteata
Sideroxylon cubense
Smilax china
Smilax glabra
Sonneratia caseolaris
Stenostomum acreanum
Stephania zippeliana
Symplocos glauca
Terminalia chebula
Teucrium scorodonia
Tinospora hainanensis
Titanotrichum oldhamii
Trapa natans var. bicornis
Triadica sebifera
Uvaria littoralis
Vaccinium dunalianum
Vaccinium macrocarpon
Vellozia streptophylla
Veronica anagallis
Veronica polita
Vismia micrantha
Vismia parviflora
Waitzia acuminata
Wrightia tinctoria
Xyris indica

Cross-Links

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PubChem 8742
NPASS NPC47844
LOTUS LTS0003899
wikiData Q410830