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Geclosporin

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 87e039f9-9e9a-41a4-8709-55c6237c7c34
Taxonomy Organic acids and derivatives > Peptidomimetics > Peptoid-peptide hybrids > Cyclosporins
IUPAC Name (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-30-propyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
SMILES (Canonical) CCCC1C(=O)N(CC(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1)C(C(C)CC=CC)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C
SMILES (Isomeric) CCC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C
InChI InChI=1S/C63H113N11O12/c1-25-27-29-41(15)53(76)52-57(80)66-44(28-26-2)59(82)68(18)34-49(75)69(19)45(30-35(3)4)56(79)67-50(39(11)12)62(85)70(20)46(31-36(5)6)55(78)64-42(16)54(77)65-43(17)58(81)71(21)47(32-37(7)8)60(83)72(22)48(33-38(9)10)61(84)73(23)51(40(13)14)63(86)74(52)24/h25,27,35-48,50-53,76H,26,28-34H2,1-24H3,(H,64,78)(H,65,77)(H,66,80)(H,67,79)/b27-25+/t41-,42+,43-,44+,45+,46+,47+,48+,50+,51+,52+,53-/m1/s1
InChI Key ZMKGDQSIRSGUDJ-VSROPUKISA-N
Popularity 170 references in papers

Physical and Chemical Properties

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Molecular Formula C63H113N11O12
Molecular Weight 1216.60 g/mol
Exact Mass 1215.85701808 g/mol
Topological Polar Surface Area (TPSA) 279.00 Ų
XlogP 7.90
Atomic LogP (AlogP) 3.66
H-Bond Acceptor 12
H-Bond Donor 5
Rotatable Bonds 16

Synonyms

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Cyclosporin G
74436-00-3
cyclosporine G
Geclosporin [INN]
Cyclosporin-g
Cyclosporin A, 7-L-norvaline-
UA3JNW70T9
SDZ-37-325
(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-30-propyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
OG-37-325
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Geclosporin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5454 54.54%
Caco-2 - 0.8581 85.81%
Blood Brain Barrier - 0.9250 92.50%
Human oral bioavailability - 0.8714 87.14%
Subcellular localzation Mitochondria 0.6572 65.72%
OATP2B1 inhibitior - 0.8563 85.63%
OATP1B1 inhibitior - 0.6473 64.73%
OATP1B3 inhibitior - 0.4140 41.40%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.9619 96.19%
P-glycoprotein inhibitior + 0.7432 74.32%
P-glycoprotein substrate + 0.8127 81.27%
CYP3A4 substrate + 0.7668 76.68%
CYP2C9 substrate - 0.8284 82.84%
CYP2D6 substrate - 0.8475 84.75%
CYP3A4 inhibition - 0.5117 51.17%
CYP2C9 inhibition - 0.9198 91.98%
CYP2C19 inhibition - 0.9047 90.47%
CYP2D6 inhibition - 0.9321 93.21%
CYP1A2 inhibition - 0.9147 91.47%
CYP2C8 inhibition + 0.5862 58.62%
CYP inhibitory promiscuity - 0.9967 99.67%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.8100 81.00%
Carcinogenicity (trinary) Non-required 0.5990 59.90%
Eye corrosion - 0.9853 98.53%
Eye irritation - 0.8990 89.90%
Skin irritation - 0.7728 77.28%
Skin corrosion - 0.9009 90.09%
Ames mutagenesis - 0.5670 56.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4077 40.77%
Micronuclear + 0.7500 75.00%
Hepatotoxicity + 0.8307 83.07%
skin sensitisation - 0.8851 88.51%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity - 0.6627 66.27%
Acute Oral Toxicity (c) III 0.7586 75.86%
Estrogen receptor binding + 0.7797 77.97%
Androgen receptor binding + 0.7273 72.73%
Thyroid receptor binding + 0.6453 64.53%
Glucocorticoid receptor binding + 0.7232 72.32%
Aromatase binding + 0.6040 60.40%
PPAR gamma + 0.8046 80.46%
Honey bee toxicity - 0.7786 77.86%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.7100 71.00%
Fish aquatic toxicity - 0.6528 65.28%

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
CHEMBL1949 P62937 Cyclophilin A 99.48% 98.57%
CHEMBL2581 P07339 Cathepsin D 99.24% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.68% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.79% 96.09%
CHEMBL4072 P07858 Cathepsin B 93.54% 93.67%
CHEMBL321 P14780 Matrix metalloproteinase 9 90.26% 92.12%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.56% 95.56%
CHEMBL5103 Q969S8 Histone deacetylase 10 89.34% 90.08%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 88.95% 90.71%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.61% 97.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 88.11% 96.61%
CHEMBL1937 Q92769 Histone deacetylase 2 86.57% 94.75%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.38% 99.23%
CHEMBL255 P29275 Adenosine A2b receptor 84.55% 98.59%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 84.09% 90.93%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 83.92% 95.71%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.72% 85.14%
CHEMBL299 P17252 Protein kinase C alpha 83.71% 98.03%
CHEMBL3359 P21462 Formyl peptide receptor 1 83.38% 93.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.22% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.20% 89.00%
CHEMBL333 P08253 Matrix metalloproteinase-2 83.08% 96.31%
CHEMBL332 P03956 Matrix metalloproteinase-1 81.95% 94.50%
CHEMBL2072 P35499 Sodium channel protein type IV alpha subunit 81.70% 92.32%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 81.45% 96.47%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.00% 100.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.81% 99.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 80.72% 91.11%
CHEMBL4588 P22894 Matrix metalloproteinase 8 80.64% 94.66%
CHEMBL4208 P20618 Proteasome component C5 80.14% 90.00%

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.
There are no matching plants.

Cross-Links

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PubChem 6475296
LOTUS LTS0031916
wikiData Q27290967