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(1S,2S,4aR,4bR,7S,9S,9aR,10S,10aR)-2,7,9-trihydroxy-1-methyl-8-methylene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid

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 906a174e-26ef-468b-9e7c-4c066a0292fd
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > C19-gibberellins > C19-gibberellin 6-carboxylic acids
IUPAC Name (1R,2R,5S,7S,8R,9S,10R,11S,12S)-5,7,12-trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid
SMILES (Canonical) CC12C(CCC3(C1C(C45C3CCC(C4)(C(=C)C5O)O)C(=O)O)OC2=O)O
SMILES (Isomeric) C[C@@]12[C@H](CC[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@](C4)(C(=C)[C@H]5O)O)C(=O)O)OC2=O)O
InChI InChI=1S/C19H24O7/c1-8-13(21)18-7-17(8,25)5-3-9(18)19-6-4-10(20)16(2,15(24)26-19)12(19)11(18)14(22)23/h9-13,20-21,25H,1,3-7H2,2H3,(H,22,23)/t9-,10+,11-,12-,13-,16-,17+,18-,19-/m1/s1
InChI Key SISDKGXXRJQNSE-VKRREQRESA-N
Popularity 4 references in papers

Physical and Chemical Properties

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Molecular Formula C19H24O7
Molecular Weight 364.40 g/mol
Exact Mass 364.15220310 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP -0.90
Atomic LogP (AlogP) 0.22
H-Bond Acceptor 6
H-Bond Donor 4
Rotatable Bonds 1

Synonyms

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GA72
CHEBI:142023
DTXSID501106880
(1R,2R,5S,7S,8R,9S,10R,11S,12S)-5,7,12-Trihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid
(1S,2S,4aR,4bR,7S,9S,9aR,10S,10aR)-2,7,9-trihydroxy-1-methyl-8-methylidene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid
2beta,7alpha,9beta-trihydroxy-1beta-methyl-8-methylidene-13-oxo-4a,1alpha-epoxymethano-4aalpha,4bbeta-gibbane-10beta-carboxylic acid
ent-3alpha,10beta,13,15alpha-tetrahydroxy-20-norgibberell-16-ene-7,19-dioic acid 19,10-lactone
Gibbane-1,10-dicarboxylic acid, 2,4a,7,9-tetrahydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2beta,4aalpha,4bbeta,9beta,10beta)-

2D Structure

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2D Structure of (1S,2S,4aR,4bR,7S,9S,9aR,10S,10aR)-2,7,9-trihydroxy-1-methyl-8-methylene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9661 96.61%
Caco-2 - 0.5940 59.40%
Blood Brain Barrier + 0.5527 55.27%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.6919 69.19%
OATP2B1 inhibitior - 0.8627 86.27%
OATP1B1 inhibitior + 0.9184 91.84%
OATP1B3 inhibitior + 0.9312 93.12%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6592 65.92%
BSEP inhibitior - 0.9519 95.19%
P-glycoprotein inhibitior - 0.8860 88.60%
P-glycoprotein substrate - 0.7512 75.12%
CYP3A4 substrate + 0.6484 64.84%
CYP2C9 substrate - 0.8108 81.08%
CYP2D6 substrate - 0.8571 85.71%
CYP3A4 inhibition - 0.8183 81.83%
CYP2C9 inhibition - 0.8848 88.48%
CYP2C19 inhibition - 0.8876 88.76%
CYP2D6 inhibition - 0.9444 94.44%
CYP1A2 inhibition - 0.8086 80.86%
CYP2C8 inhibition - 0.6806 68.06%
CYP inhibitory promiscuity - 0.9419 94.19%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5198 51.98%
Eye corrosion - 0.9866 98.66%
Eye irritation - 0.9417 94.17%
Skin irritation + 0.4913 49.13%
Skin corrosion - 0.8775 87.75%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6605 66.05%
Micronuclear - 0.7300 73.00%
Hepatotoxicity - 0.5342 53.42%
skin sensitisation - 0.7911 79.11%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.9750 97.50%
Nephrotoxicity + 0.7940 79.40%
Acute Oral Toxicity (c) IV 0.4235 42.35%
Estrogen receptor binding + 0.8576 85.76%
Androgen receptor binding + 0.6179 61.79%
Thyroid receptor binding + 0.6459 64.59%
Glucocorticoid receptor binding + 0.7475 74.75%
Aromatase binding + 0.6178 61.78%
PPAR gamma - 0.5976 59.76%
Honey bee toxicity - 0.8925 89.25%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9902 99.02%

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 90.18% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.53% 95.56%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 86.50% 96.38%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.05% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.04% 99.23%
CHEMBL2581 P07339 Cathepsin D 83.47% 98.95%
CHEMBL340 P08684 Cytochrome P450 3A4 83.24% 91.19%
CHEMBL5028 O14672 ADAM10 83.02% 97.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.36% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.76% 93.04%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 80.16% 93.00%

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.
Helianthus annuus

Cross-Links

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PubChem 14160510
LOTUS LTS0260465
wikiData Q105253998