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12,13-Dihydroxyfumitremorgin C

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 512de4f5-22d6-4ea5-b67b-42a1048cf09a
Taxonomy Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
IUPAC Name (1R,2S,12S,15S)-1,2-dihydroxy-7-methoxy-12-(2-methylprop-1-enyl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4(9),5,7-tetraene-14,20-dione
SMILES (Canonical) CC(=CC1C2=C(C(C3(N1C(=O)C4CCCN4C3=O)O)O)C5=C(N2)C=C(C=C5)OC)C
SMILES (Isomeric) CC(=C[C@H]1C2=C([C@@H]([C@@]3(N1C(=O)[C@@H]4CCCN4C3=O)O)O)C5=C(N2)C=C(C=C5)OC)C
InChI InChI=1S/C22H25N3O5/c1-11(2)9-16-18-17(13-7-6-12(30-3)10-14(13)23-18)19(26)22(29)21(28)24-8-4-5-15(24)20(27)25(16)22/h6-7,9-10,15-16,19,23,26,29H,4-5,8H2,1-3H3/t15-,16-,19-,22+/m0/s1
InChI Key CPHRCQUGNAGVIB-FWJAZRMLSA-N
Popularity 8 references in papers

Physical and Chemical Properties

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Molecular Formula C22H25N3O5
Molecular Weight 411.50 g/mol
Exact Mass 411.17942091 g/mol
Topological Polar Surface Area (TPSA) 106.00 Ų
XlogP 1.10
Atomic LogP (AlogP) 1.75
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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12alpha,13alpha-dihydroxyfumitremorgin C
111427-99-7
(5aR,6S,12S,14aS)-5a,6-dihydroxy-9-methoxy-12-(2-methylprop-1-en-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione
(5aR,6S,12S,14aS)-5a,6-Dihydroxy-9-methoxy-12-(2-methylprop-1-en-1-yl)-1,2,3,5a,6,14a-hexahydropyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14(11H,12H)-dione
CHEMBL3884139
CHEBI:72764
DTXSID001305297
BS-1142
C20605
Q27140131
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of 12,13-Dihydroxyfumitremorgin C

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6070 60.70%
Caco-2 + 0.6073 60.73%
Blood Brain Barrier - 0.9250 92.50%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.7719 77.19%
OATP2B1 inhibitior - 0.7128 71.28%
OATP1B1 inhibitior + 0.8732 87.32%
OATP1B3 inhibitior + 0.9203 92.03%
MATE1 inhibitior - 0.8200 82.00%
OCT2 inhibitior - 0.8317 83.17%
BSEP inhibitior + 0.9366 93.66%
P-glycoprotein inhibitior - 0.4816 48.16%
P-glycoprotein substrate + 0.5473 54.73%
CYP3A4 substrate + 0.6949 69.49%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7865 78.65%
CYP3A4 inhibition - 0.9076 90.76%
CYP2C9 inhibition - 0.8376 83.76%
CYP2C19 inhibition - 0.8682 86.82%
CYP2D6 inhibition - 0.8947 89.47%
CYP1A2 inhibition - 0.6777 67.77%
CYP2C8 inhibition - 0.6098 60.98%
CYP inhibitory promiscuity - 0.7229 72.29%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6009 60.09%
Eye corrosion - 0.9879 98.79%
Eye irritation - 0.9389 93.89%
Skin irritation - 0.7721 77.21%
Skin corrosion - 0.9370 93.70%
Ames mutagenesis - 0.5470 54.70%
Human Ether-a-go-go-Related Gene inhibition - 0.5595 55.95%
Micronuclear + 0.7400 74.00%
Hepatotoxicity - 0.6187 61.87%
skin sensitisation - 0.8791 87.91%
Respiratory toxicity + 0.7889 78.89%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.7904 79.04%
Acute Oral Toxicity (c) III 0.6620 66.20%
Estrogen receptor binding + 0.7057 70.57%
Androgen receptor binding + 0.8101 81.01%
Thyroid receptor binding + 0.5492 54.92%
Glucocorticoid receptor binding + 0.6913 69.13%
Aromatase binding + 0.6781 67.81%
PPAR gamma + 0.5806 58.06%
Honey bee toxicity - 0.7681 76.81%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.8757 87.57%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.17% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 98.78% 94.45%
CHEMBL2581 P07339 Cathepsin D 98.51% 98.95%
CHEMBL1902 P62942 FK506-binding protein 1A 97.76% 97.05%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.30% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.85% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 94.92% 95.89%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 93.59% 93.40%
CHEMBL241 Q14432 Phosphodiesterase 3A 92.67% 92.94%
CHEMBL284 P27487 Dipeptidyl peptidase IV 91.13% 95.69%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.40% 97.09%
CHEMBL4208 P20618 Proteasome component C5 88.36% 90.00%
CHEMBL1937 Q92769 Histone deacetylase 2 86.85% 94.75%
CHEMBL1871 P10275 Androgen Receptor 85.98% 96.43%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.85% 94.00%
CHEMBL1951 P21397 Monoamine oxidase A 85.60% 91.49%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.51% 89.00%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 84.04% 91.03%
CHEMBL5203 P33316 dUTP pyrophosphatase 83.78% 99.18%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 82.40% 93.03%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 82.27% 82.69%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.69% 86.33%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 80.31% 86.92%

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 10001648
LOTUS LTS0112855
wikiData Q27140131