Platanic acid

Details

• Internal ID: 5e6fd504-5333-42b8-8f28-b30b8d59a194
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Oxosteroids
• IUPAC Name: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• SMILES (Canonical): CC(=O)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)O
• SMILES (Isomeric): CC(=O)[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)C)(C)C)O)C)C(=O)O
• InChI: InChI=1S/C29H46O4/c1-17(30)18-9-14-29(24(32)33)16-15-27(5)19(23(18)29)7-8-21-26(4)12-11-22(31)25(2,3)20(26)10-13-28(21,27)6/h18-23,31H,7-16H2,1-6H3,(H,32,33)/t18-,19+,20-,21+,22-,23+,26-,27+,28+,29-/m0/s1
• InChI Key: RVMPLOSJMIQORE-FUAAEJBOSA-N
• Popularity: 21 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₆O₄
• Molecular Weight: 458.70 g/mol
• Exact Mass: 458.33960994 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 6.10
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 6060-06-6
• CHEMBL80460
• CHEBI:65487
• 3beta-Hydroxy-20-oxo-30-norlupan-28-oic acid
• (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid
• SCHEMBL15918102
• DTXSID30976042
• RVMPLOSJMIQORE-FUAAEJBOSA-N
• BDBM50103962
• (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• 3-Hydroxy-20-oxonorlupan-28-oic acid, (3.beta.)
• Q27133930
• 30-Norlupan-28-oic acid, 3-hydroxy-20-oxo-, (3beta)-
• (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-Acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carboxylic acid
• (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
• 1-Acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid
• 1-Acetyl-9-hydroxy-5alpha,5beta,8,8,11alpha-pentamethylicosahydro-3rHcyclopenta[alpha]chrysene-3alpha-carboxylic Acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9861	98.61%
Caco-2	-	0.6001	60.01%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8640	86.40%
OATP2B1 inhibitior	-	0.7159	71.59%
OATP1B1 inhibitior	+	0.9289	92.89%
OATP1B3 inhibitior	+	0.8726	87.26%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7321	73.21%
BSEP inhibitior	+	0.5861	58.61%
P-glycoprotein inhibitior	-	0.8307	83.07%
P-glycoprotein substrate	-	0.8670	86.70%
CYP3A4 substrate	+	0.6933	69.33%
CYP2C9 substrate	-	0.8363	83.63%
CYP2D6 substrate	-	0.8429	84.29%
CYP3A4 inhibition	-	0.8850	88.50%
CYP2C9 inhibition	-	0.9341	93.41%
CYP2C19 inhibition	-	0.9705	97.05%
CYP2D6 inhibition	-	0.9774	97.74%
CYP1A2 inhibition	-	0.9100	91.00%
CYP2C8 inhibition	-	0.5806	58.06%
CYP inhibitory promiscuity	-	0.9828	98.28%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7308	73.08%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.9300	93.00%
Skin irritation	+	0.6930	69.30%
Skin corrosion	-	0.9283	92.83%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5302	53.02%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.8028	80.28%
skin sensitisation	-	0.7383	73.83%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7113	71.13%
Acute Oral Toxicity (c)	III	0.6009	60.09%
Estrogen receptor binding	+	0.8066	80.66%
Androgen receptor binding	+	0.7671	76.71%
Thyroid receptor binding	+	0.5726	57.26%
Glucocorticoid receptor binding	+	0.7637	76.37%
Aromatase binding	+	0.6980	69.80%
PPAR gamma	+	0.6383	63.83%
Honey bee toxicity	-	0.6768	67.68%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9920	99.20%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2047	Q96RI1	Bile acid receptor FXR	0 nM	EC50	PMID: 19911773
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	3110 nM	EC50	PMID: 19911773

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.39%	96.09%
CHEMBL204	P00734	Thrombin	91.30%	96.01%
CHEMBL340	P08684	Cytochrome P450 3A4	89.68%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.34%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.95%	96.38%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	85.70%	96.09%
CHEMBL2581	P07339	Cathepsin D	85.13%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.12%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.26%	93.00%
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	81.80%	91.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.79%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.71%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.12%	100.00%
CHEMBL5028	O14672	ADAM10	80.80%	97.50%

Plants that contains it

• Albertisia papuana
• Arbutus unedo
• Artemisia biennis
• Astragalus asper
• Aulacomnium androgynum
• Breynia fruticosa
• Cosmos pringlei
• Dahlstedtia araripensis
• Daphnopsis macrophylla
• Derris trifoliata
• Dioscorea althaeoides
• Dorstenia convexa
• Drimia maritima
• Erythrina sacleuxii
• Ficus salicifolia
• Gardneria nutans
• Glycyrrhiza lepidota
• Lafoensia glyptocarpa
• Leptospermum scoparium
• Lonchocarpus parviflorus
• Madhuca pasquieri
• Magnolia sprengeri
• Melaleuca ericifolia
• Melaleuca leucadendra
• Osteophloeum platyspermum
• Taraxacum bicorne
• Valeriana fedtschenkoi

Cross-Links

• PubChem: 64980
• NPASS: NPC30583
• ChEMBL: CHEMBL80460
• LOTUS: LTS0088243
• wikiData: Q27133930