Gardneramine

Details

Top
Internal ID 0fa1930a-86ca-45d4-8882-936d6f385ab2
Taxonomy Organoheterocyclic compounds > Indoles and derivatives > Indoles > 3-alkylindoles
IUPAC Name (12S,13S,16Z,17S)-3,4,6-trimethoxy-16-(2-methoxyethylidene)-10-oxa-8,14-diazahexacyclo[11.6.1.01,9.02,7.012,17.014,19]icosa-2(7),3,5,8-tetraene
SMILES (Canonical) COCC=C1CN2C3CC1C4C2CC35C6=C(C(=CC(=C6OC)OC)OC)N=C5OC4
SMILES (Isomeric) COC/C=C/1\CN2[C@H]3CC45C2C[C@H]1[C@@H]3COC4=NC6=C5C(=C(C=C6OC)OC)OC
InChI InChI=1S/C23H28N2O5/c1-26-6-5-12-10-25-15-9-23-18(25)7-13(12)14(15)11-30-22(23)24-20-16(27-2)8-17(28-3)21(29-4)19(20)23/h5,8,13-15,18H,6-7,9-11H2,1-4H3/b12-5+/t13-,14+,15+,18?,23?/m1/s1
InChI Key RIMDDIPKIZTBHU-KPDHXFAYSA-N
Popularity 2 references in papers

Physical and Chemical Properties

Top
Molecular Formula C23H28N2O5
Molecular Weight 412.50 g/mol
Exact Mass 412.19982200 g/mol
Topological Polar Surface Area (TPSA) 61.80 Ų
XlogP 1.30
Atomic LogP (AlogP) 2.69
H-Bond Acceptor 7
H-Bond Donor 0
Rotatable Bonds 5

Synonyms

Top
34274-91-4
(12S,13S,16Z,17S)-3,4,6-trimethoxy-16-(2-methoxyethylidene)-10-oxa-8,14-diazahexacyclo[11.6.1.01,9.02,7.012,17.014,19]icosa-2(7),3,5,8-tetraene
BRN 1095912
Gardneramine oxindole, 1,2-didehydro-2-deoxo-17-deoxy-2,17-epoxy-
1,2-Didehydro-2-deoxo-17-deoxy-2,17-epoxygardneramine oxindole

2D Structure

Top
2D Structure of Gardneramine

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9544 95.44%
Caco-2 + 0.6985 69.85%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.5307 53.07%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9043 90.43%
OATP1B3 inhibitior + 0.9352 93.52%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior + 0.8182 81.82%
P-glycoprotein inhibitior + 0.6869 68.69%
P-glycoprotein substrate + 0.6720 67.20%
CYP3A4 substrate + 0.6823 68.23%
CYP2C9 substrate - 0.5808 58.08%
CYP2D6 substrate + 0.5000 50.00%
CYP3A4 inhibition + 0.5694 56.94%
CYP2C9 inhibition - 0.7968 79.68%
CYP2C19 inhibition - 0.7645 76.45%
CYP2D6 inhibition - 0.8532 85.32%
CYP1A2 inhibition - 0.7830 78.30%
CYP2C8 inhibition + 0.7301 73.01%
CYP inhibitory promiscuity - 0.5398 53.98%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9000 90.00%
Carcinogenicity (trinary) Non-required 0.5883 58.83%
Eye corrosion - 0.9830 98.30%
Eye irritation - 0.9727 97.27%
Skin irritation - 0.7698 76.98%
Skin corrosion - 0.9280 92.80%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3607 36.07%
Micronuclear + 0.7100 71.00%
Hepatotoxicity + 0.5284 52.84%
skin sensitisation - 0.8247 82.47%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity + 0.6588 65.88%
Acute Oral Toxicity (c) III 0.6080 60.80%
Estrogen receptor binding + 0.7576 75.76%
Androgen receptor binding + 0.7073 70.73%
Thyroid receptor binding + 0.6824 68.24%
Glucocorticoid receptor binding + 0.7806 78.06%
Aromatase binding + 0.5333 53.33%
PPAR gamma + 0.6365 63.65%
Honey bee toxicity - 0.7253 72.53%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity + 0.9392 93.92%

Targets

Top

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.91% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.43% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.35% 94.45%
CHEMBL5747 Q92793 CREB-binding protein 94.09% 95.12%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.40% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 91.24% 96.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.48% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 88.81% 91.11%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.20% 94.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.37% 95.56%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 84.54% 89.62%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.56% 97.14%
CHEMBL2730 P21980 Protein-glutamine gamma-glutamyltransferase 83.48% 92.38%
CHEMBL4040 P28482 MAP kinase ERK2 83.14% 83.82%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.06% 92.62%

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.
Gardneria nutans

Cross-Links

Top
PubChem 6441560
LOTUS LTS0062041
wikiData Q105236973