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Chaetoglobosin A

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 4ea19a5e-4425-4b89-91b6-d792513f00a1
Taxonomy Alkaloids and derivatives > Cytochalasans > Chaetoglobosins
IUPAC Name (1R,3E,6R,7E,9S,11E,13R,14S,16R,17S,18R,19S)-6-hydroxy-19-(1H-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.01,18.014,16]henicosa-3,7,11-triene-2,5,21-trione
SMILES (Canonical) CC1CC=CC2C3C(O3)(C(C4C2(C(=O)C=CC(=O)C(C(=C1)C)O)C(=O)NC4CC5=CNC6=CC=CC=C65)C)C
SMILES (Isomeric) C[C@H]\1C/C=C/[C@H]2[C@H]3[C@](O3)([C@H]([C@@H]4[C@@]2(C(=O)/C=C/C(=O)[C@@H](/C(=C1)/C)O)C(=O)N[C@H]4CC5=CNC6=CC=CC=C65)C)C
InChI InChI=1S/C32H36N2O5/c1-17-8-7-10-22-29-31(4,39-29)19(3)27-24(15-20-16-33-23-11-6-5-9-21(20)23)34-30(38)32(22,27)26(36)13-12-25(35)28(37)18(2)14-17/h5-7,9-14,16-17,19,22,24,27-29,33,37H,8,15H2,1-4H3,(H,34,38)/b10-7+,13-12+,18-14+/t17-,19-,22-,24-,27-,28+,29-,31+,32+/m0/s1
InChI Key OUMWCYMRLMEZJH-VOXRAUTJSA-N
Popularity 102 references in papers

Physical and Chemical Properties

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Molecular Formula C32H36N2O5
Molecular Weight 528.60 g/mol
Exact Mass 528.26242225 g/mol
Topological Polar Surface Area (TPSA) 112.00 Ų
XlogP 3.70
Atomic LogP (AlogP) 3.83
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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Chaetoglobosins
50335-03-0
NSC 366739
BRN 1097707
(1R,3E,6R,7E,9S,11E,13R,14S,16R,17S,18R,19S)-6-hydroxy-19-(1H-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.01,18.014,16]henicosa-3,7,11-triene-2,5,21-trione
(13)Cytochalasa-13,17,21-triene-1,20,23-trione, 6,7-epoxy-19-hydroxy-10-(1H-indol-3-yl)-16,18-dimethyl-, (7S,13E,16S,17E,19R,21E)-
73AYL68TNX
MLS000876953
C32H36N2O5
[13]Cytochalasa-13,17,21-triene-1,20,23-trione, 6,7-epoxy-19-hydroxy-10-(1H-indol-3-yl)-16,18-dimethyl-, (7S,13E,16S,17E,19R,21E)-
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Chaetoglobosin A

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9768 97.68%
Caco-2 - 0.8179 81.79%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Plasma membrane 0.4668 46.68%
OATP2B1 inhibitior - 0.8580 85.80%
OATP1B1 inhibitior + 0.8421 84.21%
OATP1B3 inhibitior + 0.9313 93.13%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.9919 99.19%
P-glycoprotein inhibitior + 0.7889 78.89%
P-glycoprotein substrate + 0.7269 72.69%
CYP3A4 substrate + 0.7230 72.30%
CYP2C9 substrate - 0.8000 80.00%
CYP2D6 substrate - 0.8500 85.00%
CYP3A4 inhibition - 0.6489 64.89%
CYP2C9 inhibition - 0.6702 67.02%
CYP2C19 inhibition - 0.6958 69.58%
CYP2D6 inhibition - 0.8639 86.39%
CYP1A2 inhibition - 0.7710 77.10%
CYP2C8 inhibition + 0.7155 71.55%
CYP inhibitory promiscuity + 0.7000 70.00%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Danger 0.4189 41.89%
Eye corrosion - 0.9879 98.79%
Eye irritation - 0.9578 95.78%
Skin irritation - 0.7637 76.37%
Skin corrosion - 0.9285 92.85%
Ames mutagenesis - 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7540 75.40%
Micronuclear + 0.8100 81.00%
Hepatotoxicity + 0.5426 54.26%
skin sensitisation - 0.8363 83.63%
Respiratory toxicity + 0.8667 86.67%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.8375 83.75%
Nephrotoxicity + 0.4576 45.76%
Acute Oral Toxicity (c) II 0.7287 72.87%
Estrogen receptor binding + 0.7683 76.83%
Androgen receptor binding + 0.6562 65.62%
Thyroid receptor binding + 0.6925 69.25%
Glucocorticoid receptor binding + 0.8135 81.35%
Aromatase binding + 0.6387 63.87%
PPAR gamma + 0.7505 75.05%
Honey bee toxicity - 0.6658 66.58%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.5353 53.53%
Fish aquatic toxicity + 0.9268 92.68%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL4040 P28482 MAP kinase ERK2 794.3 nM
 Potency
 via Super-PRED
CHEMBL1293224 P10636 Microtubule-associated protein tau 891.3 nM
 Potency
 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.58% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 97.47% 95.56%
CHEMBL3310 Q96DB2 Histone deacetylase 11 96.47% 88.56%
CHEMBL2581 P07339 Cathepsin D 95.47% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.73% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.51% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 92.19% 99.23%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.94% 94.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 90.30% 92.62%
CHEMBL3401 O75469 Pregnane X receptor 90.25% 94.73%
CHEMBL3192 Q9BY41 Histone deacetylase 8 89.71% 93.99%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.53% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.18% 97.09%
CHEMBL213 P08588 Beta-1 adrenergic receptor 87.92% 95.56%
CHEMBL5103 Q969S8 Histone deacetylase 10 87.16% 90.08%
CHEMBL1937 Q92769 Histone deacetylase 2 86.08% 94.75%
CHEMBL255 P29275 Adenosine A2b receptor 84.92% 98.59%
CHEMBL2996 Q05655 Protein kinase C delta 84.32% 97.79%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.98% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.85% 100.00%
CHEMBL2693 Q9UIQ6 Cystinyl aminopeptidase 83.48% 97.64%
CHEMBL5805 Q9NR97 Toll-like receptor 8 83.09% 96.25%
CHEMBL4530 P00488 Coagulation factor XIII 82.01% 96.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.04% 86.33%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 80.87% 96.90%

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.
Ginkgo biloba
Gymnosporia acuminata

Cross-Links

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PubChem 6438437
NPASS NPC57690
LOTUS LTS0133104
wikiData Q15410885