Haemanthidine

Details

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Internal ID 61b73fa5-78a2-4936-ad81-eca08e0a1118
Taxonomy Alkaloids and derivatives > Amaryllidaceae alkaloids > Crinine- and Haemanthamine-type amaryllidaceae alkaloids
IUPAC Name 15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraene-11,18-diol
SMILES (Canonical) COC1CC2C3(C=C1)C(CN2C(C4=CC5=C(C=C34)OCO5)O)O
SMILES (Isomeric) COC1CC2C3(C=C1)C(CN2C(C4=CC5=C(C=C34)OCO5)O)O
InChI InChI=1S/C17H19NO5/c1-21-9-2-3-17-11-6-13-12(22-8-23-13)5-10(11)16(20)18(7-15(17)19)14(17)4-9/h2-3,5-6,9,14-16,19-20H,4,7-8H2,1H3
InChI Key ZSTPNQLNQBRLQF-UHFFFAOYSA-N
Popularity 8 references in papers

Physical and Chemical Properties

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Molecular Formula C17H19NO5
Molecular Weight 317.34 g/mol
Exact Mass 317.12632271 g/mol
Topological Polar Surface Area (TPSA) 71.40 Ų
XlogP 0.70
Atomic LogP (AlogP) 0.68
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 1

Synonyms

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Hemanthidine
Crinan-6,11-diol, 1,2-didehydro-3-methoxy-, (3beta,5alpha,6beta,11R,13beta,19alpha)-
ZSTPNQLNQBRLQF-UHFFFAOYSA-N
4a.beta.,5.alpha.,11b.alpha.-Crinan-6.beta.,12-diol, 1,2-didehydro-3.beta.-methoxy-, (12R)-
Crinan-6,11-diol, 1,2-didehydro-3-methoxy-, (3.beta.,5.alpha.,6.beta.,11R,13.beta.,19.alpha.)-
3-Methoxy-1,2-didehydrocrinan-6,11-diol #
3H,6H-5,11b-Ethano[1,3]dioxolo[4,5-j]phenanthridine, crinan-6,11-diol deriv.
15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraene-11,18-diol
Crinan-7,18-diol, 1,2-didehydro-3-methoxy-, (3.beta.,5.beta.,6.alpha.,7.beta.,17.alpha.,18R)-

2D Structure

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2D Structure of Haemanthidine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9528 95.28%
Caco-2 + 0.7821 78.21%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Lysosomes 0.4606 46.06%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9165 91.65%
OATP1B3 inhibitior + 0.9504 95.04%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.5613 56.13%
P-glycoprotein inhibitior - 0.8912 89.12%
P-glycoprotein substrate - 0.6922 69.22%
CYP3A4 substrate + 0.6128 61.28%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7055 70.55%
CYP3A4 inhibition - 0.7948 79.48%
CYP2C9 inhibition - 0.8084 80.84%
CYP2C19 inhibition - 0.6104 61.04%
CYP2D6 inhibition - 0.6187 61.87%
CYP1A2 inhibition - 0.8104 81.04%
CYP2C8 inhibition - 0.8483 84.83%
CYP inhibitory promiscuity - 0.7052 70.52%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5680 56.80%
Eye corrosion - 0.9868 98.68%
Eye irritation - 0.9667 96.67%
Skin irritation - 0.7658 76.58%
Skin corrosion - 0.9286 92.86%
Ames mutagenesis - 0.5137 51.37%
Human Ether-a-go-go-Related Gene inhibition - 0.5640 56.40%
Micronuclear + 0.7400 74.00%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.8231 82.31%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.9375 93.75%
Nephrotoxicity + 0.5074 50.74%
Acute Oral Toxicity (c) III 0.6261 62.61%
Estrogen receptor binding + 0.5780 57.80%
Androgen receptor binding + 0.6745 67.45%
Thyroid receptor binding + 0.7313 73.13%
Glucocorticoid receptor binding + 0.5821 58.21%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.5611 56.11%
Honey bee toxicity - 0.7562 75.62%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5700 57.00%
Fish aquatic toxicity + 0.7074 70.74%

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
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 98.49% 96.77%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.67% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.50% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.01% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 92.40% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.89% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.60% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.63% 89.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.81% 92.62%
CHEMBL4208 P20618 Proteasome component C5 84.70% 90.00%
CHEMBL5311 P37023 Serine/threonine-protein kinase receptor R3 84.09% 82.67%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 83.52% 82.38%
CHEMBL2581 P07339 Cathepsin D 82.91% 98.95%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 82.41% 90.24%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.44% 95.89%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.42% 90.71%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.00% 100.00%

Cross-Links

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PubChem 544807
LOTUS LTS0001591
wikiData Q105382717