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2H-1,4a-(Epoxymethano)naphthalene-4-carboxylic acid, 1,5,6,7,8,8a-hexahydro-3-[(1Z)-2-(methoxycarbonyl)-3-methyl-1-butenyl]-8,8-dimethyl-2,9-dioxo-, (1R,4aS,8aR)-rel-(+)-

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 2d555fde-b650-4287-9f72-463be044c67e
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
IUPAC Name (1R,6S,7S)-9-[(Z)-2-methoxycarbonyl-3-methylbut-1-enyl]-5,5-dimethyl-8,11-dioxo-12-oxatricyclo[5.3.2.01,6]dodec-9-ene-10-carboxylic acid
SMILES (Canonical) CC(C)C(=CC1=C(C23CCCC(C2C(C1=O)OC3=O)(C)C)C(=O)O)C(=O)OC
SMILES (Isomeric) CC(C)/C(=C/C1=C([C@@]23CCCC([C@@H]2[C@@H](C1=O)OC3=O)(C)C)C(=O)O)/C(=O)OC
InChI InChI=1S/C21H26O7/c1-10(2)11(18(25)27-5)9-12-13(17(23)24)21-8-6-7-20(3,4)16(21)15(14(12)22)28-19(21)26/h9-10,15-16H,6-8H2,1-5H3,(H,23,24)/b11-9-/t15-,16+,21+/m1/s1
InChI Key CAXSJVGHYYBJKT-GVXCCEMESA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H26O7
Molecular Weight 390.40 g/mol
Exact Mass 390.16785316 g/mol
Topological Polar Surface Area (TPSA) 107.00 Ų
XlogP 3.20
Atomic LogP (AlogP) 2.44
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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Rosmic acid
(1R,6S,7S)-9-[(Z)-2-Methoxycarbonyl-3-methylbut-1-enyl]-5,5-dimethyl-8,11-dioxo-12-oxatricyclo[5.3.2.01,6]dodec-9-ene-10-carboxylic acid
2H-1,4a-(Epoxymethano)naphthalene-4-carboxylic acid, 1,5,6,7,8,8a-hexahydro-3-[(1Z)-2-(methoxycarbonyl)-3-methyl-1-butenyl]-8,8-dimethyl-2,9-dioxo-, (1R,4aS,8aR)-rel-(+)-
DTXSID001099153
AKOS040735426

2D Structure

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2D Structure of 2H-1,4a-(Epoxymethano)naphthalene-4-carboxylic acid, 1,5,6,7,8,8a-hexahydro-3-[(1Z)-2-(methoxycarbonyl)-3-methyl-1-butenyl]-8,8-dimethyl-2,9-dioxo-, (1R,4aS,8aR)-rel-(+)-

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9803 98.03%
Caco-2 + 0.5686 56.86%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7318 73.18%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8670 86.70%
OATP1B3 inhibitior + 0.8691 86.91%
MATE1 inhibitior - 0.7600 76.00%
OCT2 inhibitior - 0.5750 57.50%
BSEP inhibitior - 0.8820 88.20%
P-glycoprotein inhibitior - 0.5983 59.83%
P-glycoprotein substrate - 0.7732 77.32%
CYP3A4 substrate + 0.6120 61.20%
CYP2C9 substrate - 0.8325 83.25%
CYP2D6 substrate - 0.9113 91.13%
CYP3A4 inhibition - 0.6869 68.69%
CYP2C9 inhibition - 0.6748 67.48%
CYP2C19 inhibition - 0.7224 72.24%
CYP2D6 inhibition - 0.8851 88.51%
CYP1A2 inhibition + 0.5620 56.20%
CYP2C8 inhibition - 0.7794 77.94%
CYP inhibitory promiscuity - 0.7885 78.85%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.5359 53.59%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.9062 90.62%
Skin irritation - 0.5763 57.63%
Skin corrosion - 0.9174 91.74%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7613 76.13%
Micronuclear - 0.6900 69.00%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.7272 72.72%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.7444 74.44%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity + 0.5637 56.37%
Acute Oral Toxicity (c) III 0.5592 55.92%
Estrogen receptor binding + 0.7429 74.29%
Androgen receptor binding + 0.5704 57.04%
Thyroid receptor binding + 0.5716 57.16%
Glucocorticoid receptor binding + 0.7724 77.24%
Aromatase binding + 0.6008 60.08%
PPAR gamma + 0.6780 67.80%
Honey bee toxicity - 0.8419 84.19%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9913 99.13%

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 97.59% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.77% 94.45%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 91.50% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.30% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 89.61% 97.25%
CHEMBL3401 O75469 Pregnane X receptor 88.45% 94.73%
CHEMBL340 P08684 Cytochrome P450 3A4 85.61% 91.19%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 85.08% 93.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.80% 96.09%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.23% 92.62%
CHEMBL5028 O14672 ADAM10 83.48% 97.50%
CHEMBL2581 P07339 Cathepsin D 83.18% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.13% 85.14%
CHEMBL221 P23219 Cyclooxygenase-1 82.87% 90.17%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.53% 95.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.16% 97.09%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.99% 91.07%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.73% 97.14%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.68% 93.56%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.48% 93.04%

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.
Rosmarinus officinalis

Cross-Links

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PubChem 102586055
LOTUS LTS0063094
wikiData Q104952030