Aucubin

Details

Top
Internal ID e15b2368-7531-4df0-9672-ecd8b14ce270
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) C1=COC(C2C1C(C=C2CO)O)OC3C(C(C(C(O3)CO)O)O)O
SMILES (Isomeric) C1=CO[C@H]([C@H]2[C@@H]1[C@@H](C=C2CO)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
InChI InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1
InChI Key RJWJHRPNHPHBRN-FKVJWERZSA-N
Popularity 787 references in papers

Physical and Chemical Properties

Top
Molecular Formula C15H22O9
Molecular Weight 346.33 g/mol
Exact Mass 346.12638228 g/mol
Topological Polar Surface Area (TPSA) 149.00 Ų
XlogP -3.00
Atomic LogP (AlogP) -2.80
H-Bond Acceptor 9
H-Bond Donor 6
Rotatable Bonds 4

Synonyms

Top
479-98-1
rhinanthin
Aucuboside
UNII-2G52GS8UML
EINECS 207-540-8
2G52GS8UML
NSC 407293
Rhimantin
CHEBI:69796
1,4a,5,7a-Tetrahydro-5-hydroxy-7-hydroxymethylcyclopenta(c)pyran-1-yl-beta-D-glucopyranoside
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top
2D Structure of Aucubin

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6717 67.17%
Caco-2 - 0.8583 85.83%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.5905 59.05%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8588 85.88%
OATP1B3 inhibitior + 0.9631 96.31%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.9839 98.39%
P-glycoprotein inhibitior - 0.8972 89.72%
P-glycoprotein substrate - 0.8967 89.67%
CYP3A4 substrate + 0.5175 51.75%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8272 82.72%
CYP3A4 inhibition - 0.9416 94.16%
CYP2C9 inhibition - 0.9116 91.16%
CYP2C19 inhibition - 0.7815 78.15%
CYP2D6 inhibition - 0.8755 87.55%
CYP1A2 inhibition - 0.8639 86.39%
CYP2C8 inhibition - 0.7692 76.92%
CYP inhibitory promiscuity - 0.6978 69.78%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6579 65.79%
Eye corrosion - 0.9890 98.90%
Eye irritation - 0.9388 93.88%
Skin irritation - 0.8209 82.09%
Skin corrosion - 0.9609 96.09%
Ames mutagenesis - 0.5691 56.91%
Human Ether-a-go-go-Related Gene inhibition - 0.5847 58.47%
Micronuclear - 0.7441 74.41%
Hepatotoxicity - 0.9125 91.25%
skin sensitisation - 0.8878 88.78%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.6444 64.44%
Mitochondrial toxicity - 0.5750 57.50%
Nephrotoxicity + 0.5530 55.30%
Acute Oral Toxicity (c) IV 0.4268 42.68%
Estrogen receptor binding - 0.7841 78.41%
Androgen receptor binding - 0.5988 59.88%
Thyroid receptor binding - 0.5308 53.08%
Glucocorticoid receptor binding - 0.7675 76.75%
Aromatase binding + 0.5487 54.87%
PPAR gamma + 0.5840 58.40%
Honey bee toxicity - 0.7774 77.74%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.7150 71.50%
Fish aquatic toxicity - 0.5621 56.21%

Targets

Top

Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL1287622 Q9Y468 Lethal(3)malignant brain tumor-like protein 1 63.1 nM
63.1 nM
Potency
Potency
via CMAUP
via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.14% 91.11%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 89.59% 86.92%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.72% 96.09%
CHEMBL3401 O75469 Pregnane X receptor 82.41% 94.73%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.55% 97.09%
CHEMBL3714130 P46095 G-protein coupled receptor 6 81.05% 97.36%

Plants that contains it

Top
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.
Allium stipitatum
Alstonia longifolia
Angelonia integerrima
Angiopteris evecta
Antirrhinum majus
Aragoa cundinamarcensis
Artemisia argentea
Asphodeline damascena
Aucuba japonica
Aureolaria flava
Bartsia alpina
Bletilla striata
Brodiaea californica
Broussonetia papyrifera
Buddleja albiflora
Buddleja cordata
Buddleja globosa
Buddleja parviflora
Buddleja sessiliflora
Campylanthus glaber
Castilleja miniata
Castilleja rhexifolia
Castilleja sulphurea
Castilleja tenuiflora
Catalpa ovata
Clerodendrum thomsoniae
Cordylanthus wrightii
Crescentia cujete
Cyathula tomentosa
Dimorphotheca fruticosa
Echinostephia aculeata
Eucalyptus kitsoniana
Eucommia ulmoides
Euphorbia antiquorum
Euphrasia nemorosa
Euphrasia salisburgensis
Exochorda racemosa subsp. giraldii
Garcinia subelliptica
Gentiana kurroo
Glinus oppositifolius
Globularia bisnagarica
Globularia cordifolia
Globularia dumulosa
Globularia nudicaulis
Globularia orientalis
Globularia trichosantha
Hemionitis lemmonii
Himantoglossum hircinum
Hypericum reflexum
Jamesbrittenia dissecta
Juncus effusus
Kandelia candel
Kopsia arborea
Lagotis brevituba
Lagotis integrifolia
Lagotis stolonifera
Lathraea squamaria
Lepidophorum repandum
Linaria macroura
Linaria vulgaris
Markhamia stipulata
Melampyrum arvense
Melampyrum chlorostachyum
Monochasma savateri
Myristica malabarica
Myroxylon peruiferum
Nicotiana alata
Odontites vernus
Parentucellia viscosa
Paulownia tomentosa
Pedicularis artselaeri
Pedicularis chinensis
Pedicularis groenlandica
Pedicularis kansuensis
Pedicularis longiflora
Pedicularis muscicola
Pedicularis nordmanniana
Pedicularis palustris
Pedicularis plicata
Pedicularis rex
Pedicularis semitorta
Pedicularis striata
Pedicularis verticillata
Penstemon auriberbis
Penstemon barbatus
Penstemon barrettiae
Penstemon ovatus
Penstemon rydbergii
Penstemon serrulatus
Phtheirospermum japonicum
Plagiomnium cuspidatum
Plantago alpina
Plantago asiatica
Plantago cornuti
Plantago depressa
Plantago lagopus
Plantago lanceolata
Plantago loeflingii
Plantago major
Plantago media
Plantago myosuros
Plantago patagonica
Plantago rhodosperma
Platycodon grandiflorus
Plectranthus lanuginosus
Populus yunnanensis
Premna microphylla
Rehmannia glutinosa
Rhodanthe maryonii
Rhododendron campylocarpum
Sagina japonica
Scabiosa comosa
Scapania aequiloba
Scrophularia buergeriana
Scrophularia canina
Scrophularia ilwensis
Scrophularia ningpoensis
Scrophularia nodosa
Scrophularia racemosa
Scrophularia scorodonia
Senecio sandersonii
Sideritis soluta
Sideritis trojana
Sidneya tenuifolia
Solanum dulcamara
Spartium junceum
Stachys palustris
Titanotrichum oldhamii
Toddalia asiatica
Utricularia australis
Vachellia lasiopetala
Verbascum cheiranthifolium
Verbascum dentifolium
Verbascum georgicum
Verbascum lychnitis
Verbascum macrurum
Verbascum nigrum
Verbascum phlomoides
Verbascum pyroliforme subsp. dudleyanum
Verbascum sinuatum
Verbascum spinosum
Verbascum thapsus
Verbascum undulatum
Verbascum wiedemannianum
Verbena officinalis
Veronica alpina
Veronica anagallis-aquatica
Veronica austriaca
Veronica besseya
Veronica filiformis
Veronica hederifolia
Veronica lavaudiana
Veronica longifolia
Veronica officinalis
Veronica orientalis
Veronica persica
Veronica pulvinaris
Veronica turrilliana
Vinca minor
Vitex agnus-castus
Vitex gardneriana
Vitex negundo

Cross-Links

Top
PubChem 91458
NPASS NPC136699
ChEMBL CHEMBL514882
LOTUS LTS0010822
wikiData Q418014