PlantaeDB Logo
Login Sign-up

Dihydromacarpine

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

Top
Internal ID ca4ad510-578c-4b2a-be7e-c195165a84c3
Taxonomy Alkaloids and derivatives > Benzophenanthridine alkaloids > Dihydrobenzophenanthridine alkaloids
IUPAC Name 11,15-dimethoxy-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14,16,21-octaene
SMILES (Canonical) CN1CC2=C3C(=CC(=C2C4=C1C5=CC6=C(C=C5C(=C4)OC)OCO6)OC)OCO3
SMILES (Isomeric) CN1CC2=C3C(=CC(=C2C4=C1C5=CC6=C(C=C5C(=C4)OC)OCO6)OC)OCO3
InChI InChI=1S/C22H19NO6/c1-23-8-14-20(18(25-3)7-19-22(14)29-10-28-19)13-6-15(24-2)11-4-16-17(27-9-26-16)5-12(11)21(13)23/h4-7H,8-10H2,1-3H3
InChI Key RTVFIUBAXAZKSU-UHFFFAOYSA-N
Popularity 3 references in papers

Physical and Chemical Properties

Top
Molecular Formula C22H19NO6
Molecular Weight 393.40 g/mol
Exact Mass 393.12123733 g/mol
Topological Polar Surface Area (TPSA) 58.60 Ų
XlogP 4.10
Atomic LogP (AlogP) 3.93
H-Bond Acceptor 7
H-Bond Donor 0
Rotatable Bonds 2

Synonyms

Top
77785-12-7
11,15-dimethoxy-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14,16,21-octaene
5,7-dimethoxy-13-methyl-13,14-dihydro-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridine
C05316
SCHEMBL891671
CHEBI:18029
DTXSID50331513
Q3707631
13,14-Dihydro-5,7-dimethoxy-13-methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridine

2D Structure

Top
2D Structure of Dihydromacarpine

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8888 88.88%
Caco-2 + 0.9019 90.19%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Lysosomes 0.5169 51.69%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9425 94.25%
OATP1B3 inhibitior + 0.9450 94.50%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.9304 93.04%
P-glycoprotein inhibitior + 0.7989 79.89%
P-glycoprotein substrate - 0.5892 58.92%
CYP3A4 substrate + 0.5361 53.61%
CYP2C9 substrate - 0.7965 79.65%
CYP2D6 substrate + 0.4942 49.42%
CYP3A4 inhibition + 0.6636 66.36%
CYP2C9 inhibition - 0.6996 69.96%
CYP2C19 inhibition + 0.8331 83.31%
CYP2D6 inhibition + 0.7540 75.40%
CYP1A2 inhibition + 0.7137 71.37%
CYP2C8 inhibition - 0.6851 68.51%
CYP inhibitory promiscuity + 0.7508 75.08%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.4498 44.98%
Eye corrosion - 0.9861 98.61%
Eye irritation - 0.8085 80.85%
Skin irritation - 0.8088 80.88%
Skin corrosion - 0.9477 94.77%
Ames mutagenesis + 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8232 82.32%
Micronuclear + 0.7000 70.00%
Hepatotoxicity + 0.7000 70.00%
skin sensitisation - 0.8369 83.69%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.7778 77.78%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity + 0.5747 57.47%
Acute Oral Toxicity (c) III 0.7250 72.50%
Estrogen receptor binding + 0.9084 90.84%
Androgen receptor binding - 0.4828 48.28%
Thyroid receptor binding + 0.6747 67.47%
Glucocorticoid receptor binding + 0.9067 90.67%
Aromatase binding + 0.6188 61.88%
PPAR gamma + 0.6678 66.78%
Honey bee toxicity - 0.7845 78.45%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity + 0.8484 84.84%

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
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 99.55% 96.77%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.19% 96.09%
CHEMBL4225 P49760 Dual specificity protein kinase CLK2 92.76% 80.96%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 91.48% 93.40%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.48% 86.33%
CHEMBL4208 P20618 Proteasome component C5 91.08% 90.00%
CHEMBL3192 Q9BY41 Histone deacetylase 8 90.71% 93.99%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.13% 95.56%
CHEMBL5747 Q92793 CREB-binding protein 89.95% 95.12%
CHEMBL2581 P07339 Cathepsin D 89.49% 98.95%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 89.16% 92.62%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 88.40% 91.11%
CHEMBL2047 Q96RI1 Bile acid receptor FXR 87.98% 96.10%
CHEMBL5311 P37023 Serine/threonine-protein kinase receptor R3 86.89% 82.67%
CHEMBL2535 P11166 Glucose transporter 86.63% 98.75%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 86.35% 96.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.30% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.73% 89.00%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 85.58% 89.62%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.41% 94.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.69% 95.89%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 83.13% 82.38%
CHEMBL2413 P32246 C-C chemokine receptor type 1 82.67% 89.50%
CHEMBL4835 P00338 L-lactate dehydrogenase A chain 82.47% 95.34%
CHEMBL4940 P07195 L-lactate dehydrogenase B chain 81.56% 95.53%

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.
Eschscholzia californica
Thalictrum lucidum

Cross-Links

Top
PubChem 440631
LOTUS LTS0189964
wikiData Q3707631