(1R,3aS,5aS,5bR,7aS,9S,11aR,11bS,13aR,13bR)-9-hydroxy-5b,8,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a,5a-dicarboxylic acid

Details

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Internal ID ba6139d8-ae62-4362-9000-341bdcf99f87
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (1R,3aS,5aS,5bR,7aS,9S,11aR,11bS,13aR,13bR)-9-hydroxy-5b,8,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a,5a-dicarboxylic acid
SMILES (Canonical) CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C(=O)O)C)(C)C)O)C)C(=O)O
SMILES (Isomeric) CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@H]4[C@]5(CC[C@@H](C([C@H]5CC[C@]4([C@@]3(CC2)C(=O)O)C)(C)C)O)C)C(=O)O
InChI InChI=1S/C30H46O5/c1-17(2)18-9-14-29(24(32)33)15-16-30(25(34)35)19(23(18)29)7-8-21-27(5)12-11-22(31)26(3,4)20(27)10-13-28(21,30)6/h18-23,31H,1,7-16H2,2-6H3,(H,32,33)(H,34,35)/t18-,19+,20+,21-,22-,23+,27-,28+,29-,30+/m0/s1
InChI Key JWDDEDFQFOCWRN-KVWPVMAKSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C30H46O5
Molecular Weight 486.70 g/mol
Exact Mass 486.33452456 g/mol
Topological Polar Surface Area (TPSA) 94.80 Ų
XlogP 6.70
Atomic LogP (AlogP) 6.15
H-Bond Acceptor 3
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,3aS,5aS,5bR,7aS,9S,11aR,11bS,13aR,13bR)-9-hydroxy-5b,8,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a,5a-dicarboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9912 99.12%
Caco-2 - 0.6014 60.14%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability + 0.5286 52.86%
Subcellular localzation Mitochondria 0.8406 84.06%
OATP2B1 inhibitior - 0.5740 57.40%
OATP1B1 inhibitior + 0.9037 90.37%
OATP1B3 inhibitior - 0.7892 78.92%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.5353 53.53%
BSEP inhibitior + 0.6227 62.27%
P-glycoprotein inhibitior - 0.7885 78.85%
P-glycoprotein substrate - 0.7524 75.24%
CYP3A4 substrate + 0.6819 68.19%
CYP2C9 substrate - 0.8404 84.04%
CYP2D6 substrate - 0.8509 85.09%
CYP3A4 inhibition - 0.8300 83.00%
CYP2C9 inhibition - 0.9221 92.21%
CYP2C19 inhibition - 0.9527 95.27%
CYP2D6 inhibition - 0.9578 95.78%
CYP1A2 inhibition - 0.9342 93.42%
CYP2C8 inhibition + 0.4649 46.49%
CYP inhibitory promiscuity - 0.9423 94.23%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6811 68.11%
Eye corrosion - 0.9946 99.46%
Eye irritation - 0.9186 91.86%
Skin irritation + 0.6926 69.26%
Skin corrosion - 0.9471 94.71%
Ames mutagenesis - 0.7500 75.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5810 58.10%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.8125 81.25%
skin sensitisation + 0.4766 47.66%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9875 98.75%
Nephrotoxicity - 0.8604 86.04%
Acute Oral Toxicity (c) III 0.4848 48.48%
Estrogen receptor binding + 0.7421 74.21%
Androgen receptor binding + 0.7589 75.89%
Thyroid receptor binding + 0.5265 52.65%
Glucocorticoid receptor binding + 0.7769 77.69%
Aromatase binding + 0.6941 69.41%
PPAR gamma + 0.5428 54.28%
Honey bee toxicity - 0.7444 74.44%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 1.0000 100.00%

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
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 92.53% 96.38%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.18% 96.09%
CHEMBL340 P08684 Cytochrome P450 3A4 89.04% 91.19%
CHEMBL221 P23219 Cyclooxygenase-1 88.74% 90.17%
CHEMBL233 P35372 Mu opioid receptor 88.33% 97.93%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 86.17% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.68% 94.45%
CHEMBL2581 P07339 Cathepsin D 83.92% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.52% 100.00%
CHEMBL218 P21554 Cannabinoid CB1 receptor 82.90% 96.61%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.60% 93.03%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.49% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.42% 82.69%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.35% 97.25%

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.
Melaleuca rhaphiophylla

Cross-Links

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PubChem 162981744
LOTUS LTS0175487
wikiData Q105136092