Pterosterone

Details

• Internal ID: a43eca26-52db-4e5a-ba34-4cc35b25b6c7
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives
• IUPAC Name: (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,5-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• SMILES (Canonical): CC(C)C(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)O
• SMILES (Isomeric): CC(C)[C@H](C[C@H]([C@@](C)([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)C)O)O)O)O
• InChI: InChI=1S/C27H44O7/c1-14(2)18(28)12-23(32)26(5,33)22-7-9-27(34)16-10-19(29)17-11-20(30)21(31)13-24(17,3)15(16)6-8-25(22,27)4/h10,14-15,17-18,20-23,28,30-34H,6-9,11-13H2,1-5H3/t15-,17-,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1
• InChI Key: UMMBJCYNGLCGEF-OAUIFJKNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₇
• Molecular Weight: 480.60 g/mol
• Exact Mass: 480.30870374 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.71
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• 18089-44-6
• CHEBI:8629
• CHEMBL2087151
• C08838
• AC1L9BQN
• CTK0H5764
• (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,5-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• DTXSID20331641
• Q27108119
• (20R,22R,24S)-2beta,3beta,14alpha,20,22,24-Hexahydroxy-5beta-cholesta-7-ene-6-one
• (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(1R,2R,4S)-1,2,4-trihydroxy-1,5-dimethyl-hexyl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9876	98.76%
Caco-2	-	0.5239	52.39%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7639	76.39%
OATP2B1 inhibitior	-	0.8575	85.75%
OATP1B1 inhibitior	+	0.9175	91.75%
OATP1B3 inhibitior	+	0.8829	88.29%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6570	65.70%
P-glycoprotein inhibitior	-	0.6968	69.68%
P-glycoprotein substrate	+	0.5394	53.94%
CYP3A4 substrate	+	0.6782	67.82%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.8669	86.69%
CYP2C9 inhibition	-	0.8366	83.66%
CYP2C19 inhibition	-	0.7655	76.55%
CYP2D6 inhibition	-	0.9506	95.06%
CYP1A2 inhibition	-	0.9041	90.41%
CYP2C8 inhibition	-	0.7070	70.70%
CYP inhibitory promiscuity	-	0.8821	88.21%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6704	67.04%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.9435	94.35%
Skin irritation	+	0.6255	62.55%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.7470	74.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4776	47.76%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.5102	51.02%
skin sensitisation	-	0.7756	77.56%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8857	88.57%
Acute Oral Toxicity (c)	I	0.5472	54.72%
Estrogen receptor binding	+	0.7621	76.21%
Androgen receptor binding	+	0.7353	73.53%
Thyroid receptor binding	+	0.6249	62.49%
Glucocorticoid receptor binding	+	0.7371	73.71%
Aromatase binding	+	0.6251	62.51%
PPAR gamma	-	0.5204	52.04%
Honey bee toxicity	-	0.8544	85.44%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9906	99.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.66%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.44%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.06%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.53%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.36%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.19%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.95%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.02%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.05%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.42%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.55%	95.89%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	88.38%	94.78%
CHEMBL221	P23219	Cyclooxygenase-1	86.66%	90.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.81%	97.14%
CHEMBL1871	P10275	Androgen Receptor	82.35%	96.43%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.22%	90.24%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.98%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.35%	94.45%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.27%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.02%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.61%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.09%	96.90%

Plants that contains it

• Artemisia lactiflora
• Attalea phalerata
• Blandfordia punicea
• Catalpa ovata
• Citrus medica
• Crepidiastrum sonchifolium
• Dipsacus inermis
• Duguetia calycina
• Garcinia pyrifera
• Gomphrena haageana
• Greenwayodendron oliveri
• Jacaranda mimosifolia
• Ophryosporus floribundus
• Payena lucida
• Pfaffia iresinoides
• Phalaris canariensis
• Philotheca spicata
• Plumbagella micrantha
• Polypodium virginianum
• Polypodium vulgare
• Pteridium aquilinum
• Quassia indica
• Rivina humilis
• Serratula coronata subsp. coronata
• Serratula tinctoria
• Vitex scabra
• Woodwardia orientalis

Cross-Links

• PubChem: 441836
• NPASS: NPC83744
• LOTUS: LTS0204913
• wikiData: Q27108119