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Roseadine

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

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Internal ID 47111b1f-2f64-4806-91ac-c9ca4b07ad27
Taxonomy Alkaloids and derivatives > Plumeran-type alkaloids
IUPAC Name methyl (1R,10S,11R,12R)-11-acetyloxy-12-ethyl-4-[(Z)-1-[(1S,15R,16R)-16-ethyl-16-hydroxy-3,13-diazatetracyclo[11.2.2.02,10.04,9]heptadeca-2(10),4,6,8-tetraen-15-yl]-3-methoxy-3-oxoprop-1-en-2-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
SMILES (Canonical) CCC1(CN2CCC3=C(C1C(C2)C=C(C4=CC5=C(C=C4OC)N(C6C57CCN8C7C(C=CC8)(C(C6(C(=O)OC)O)OC(=O)C)CC)C)C(=O)OC)NC9=CC=CC=C39)O
SMILES (Isomeric) CC[C@@]1(CN2CCC3=C([C@@H]1[C@H](C2)/C=C(/C4=CC5=C(C=C4OC)N(C6[C@]57CCN8C7[C@@](C=CC8)([C@H]([C@@]6(C(=O)OC)O)OC(=O)C)CC)C)\C(=O)OC)NC9=CC=CC=C39)O
InChI InChI=1S/C46H56N4O9/c1-8-43-16-12-18-50-20-17-45(39(43)50)32-22-30(35(56-5)23-34(32)48(4)40(45)46(55,42(53)58-7)41(43)59-26(3)51)31(38(52)57-6)21-27-24-49-19-15-29-28-13-10-11-14-33(28)47-37(29)36(27)44(54,9-2)25-49/h10-14,16,21-23,27,36,39-41,47,54-55H,8-9,15,17-20,24-25H2,1-7H3/b31-21-/t27-,36-,39?,40?,41+,43+,44-,45+,46-/m0/s1
InChI Key JPJKITSCFHYWLR-IMQGIZBBSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C46H56N4O9
Molecular Weight 809.00 g/mol
Exact Mass 808.40472938 g/mol
Topological Polar Surface Area (TPSA) 154.00 Ų
XlogP 3.50
Atomic LogP (AlogP) 4.09
H-Bond Acceptor 12
H-Bond Donor 3
Rotatable Bonds 8

Synonyms

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NSC 304424
CHEMBL505476
Aspidospermidine-3-carboxylic acid, 4-(acetyloxyl)-6,7-didehydro-15-(2-(12-ethyl-1,2,4,5,6,7-hexahydro-12-hydroxy-3,6-ethano-3H-azocino(5,4-b)indol-5-yl)-1-(methoxycarbonyl)ethenyl)-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,15(3R,5R,6R,12R),19alpha)-

2D Structure

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2D Structure of Roseadine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8937 89.37%
Caco-2 - 0.7916 79.16%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.5006 50.06%
OATP2B1 inhibitior - 0.6234 62.34%
OATP1B1 inhibitior + 0.8409 84.09%
OATP1B3 inhibitior + 0.9039 90.39%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.9952 99.52%
P-glycoprotein inhibitior + 0.8205 82.05%
P-glycoprotein substrate + 0.9009 90.09%
CYP3A4 substrate + 0.7665 76.65%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8246 82.46%
CYP3A4 inhibition - 0.9634 96.34%
CYP2C9 inhibition - 0.8889 88.89%
CYP2C19 inhibition - 0.8918 89.18%
CYP2D6 inhibition - 0.8936 89.36%
CYP1A2 inhibition - 0.8727 87.27%
CYP2C8 inhibition + 0.5355 53.55%
CYP inhibitory promiscuity - 0.8752 87.52%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5097 50.97%
Eye corrosion - 0.9882 98.82%
Eye irritation - 0.9194 91.94%
Skin irritation - 0.7677 76.77%
Skin corrosion - 0.9374 93.74%
Ames mutagenesis - 0.8600 86.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7979 79.79%
Micronuclear + 0.7700 77.00%
Hepatotoxicity - 0.6801 68.01%
skin sensitisation - 0.8692 86.92%
Respiratory toxicity + 0.9556 95.56%
Reproductive toxicity + 0.9889 98.89%
Mitochondrial toxicity + 0.9875 98.75%
Nephrotoxicity - 0.7451 74.51%
Acute Oral Toxicity (c) III 0.6401 64.01%
Estrogen receptor binding + 0.8525 85.25%
Androgen receptor binding + 0.7893 78.93%
Thyroid receptor binding + 0.6975 69.75%
Glucocorticoid receptor binding + 0.8391 83.91%
Aromatase binding + 0.5596 55.96%
PPAR gamma + 0.8035 80.35%
Honey bee toxicity - 0.6874 68.74%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity + 0.9554 95.54%

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 99.59% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.43% 91.11%
CHEMBL2581 P07339 Cathepsin D 97.98% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.45% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.97% 95.56%
CHEMBL2535 P11166 Glucose transporter 95.47% 98.75%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.90% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.09% 86.33%
CHEMBL3192 Q9BY41 Histone deacetylase 8 90.75% 93.99%
CHEMBL5747 Q92793 CREB-binding protein 88.86% 95.12%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 88.43% 95.17%
CHEMBL5028 O14672 ADAM10 88.38% 97.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.10% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.70% 95.89%
CHEMBL2413 P32246 C-C chemokine receptor type 1 87.48% 89.50%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 86.19% 94.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.80% 97.09%
CHEMBL217 P14416 Dopamine D2 receptor 85.00% 95.62%
CHEMBL4208 P20618 Proteasome component C5 84.95% 90.00%
CHEMBL233 P35372 Mu opioid receptor 84.84% 97.93%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.54% 92.62%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 83.90% 97.50%
CHEMBL2096618 P11274 Bcr/Abl fusion protein 82.39% 85.83%
CHEMBL4302 P08183 P-glycoprotein 1 81.84% 92.98%
CHEMBL340 P08684 Cytochrome P450 3A4 81.58% 91.19%
CHEMBL4895 P30530 Tyrosine-protein kinase receptor UFO 80.61% 90.95%

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.
Catharanthus roseus
Plectranthus grandidentatus
Plectranthus sanguineus

Cross-Links

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PubChem 44559285
LOTUS LTS0110830
wikiData Q105344507