(-)-Przewalskin B

Details

• Internal ID: e28f1a08-d83d-4a92-9564-f474be819773
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (1R,4S,10R,13R)-13-hydroxy-5,5-dimethyl-15-propan-2-yl-11-oxatetracyclo[8.6.0.01,13.04,9]hexadeca-8,15-diene-12,14-dione
• SMILES (Canonical): CC(C)C1=CC23CCC4C(=CCCC4(C)C)C2OC(=O)C3(C1=O)O
• SMILES (Isomeric): CC(C)C1=C[C@]23CC[C@@H]4C(=CCCC4(C)C)[C@H]2OC(=O)[C@@]3(C1=O)O
• InChI: InChI=1S/C20H26O4/c1-11(2)13-10-19-9-7-14-12(6-5-8-18(14,3)4)16(19)24-17(22)20(19,23)15(13)21/h6,10-11,14,16,23H,5,7-9H2,1-4H3/t14-,16-,19-,20-/m1/s1
• InChI Key: XENNDAKNPKZKFC-BGRCLHOASA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.95
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• B5MGR8G3HH
• Przewalskin B
• UNII-B5MGR8G3HH
• 924896-96-8
• (4bR,6aR,9aR,11aS)-1,3,4b,10,11,11a-Hexahydro-6a-hydroxy-1,1-dimethyl-8-(1-methylethyl)-2H,6H-cyclopenta(c)naphtha(1,2-b)furan-6,7(6aH)-dione
• (?)?Przewalskin B
• PRZEWALSKIN B [MI]
• (4BR,6AR,9AR,11AS)-1,3,4B,10,11,11A-HEXAHYDRO-6A-HYDROXY-1,1-DIMETHYL-8-(1-METHYLETHYL)-2H,6H-CYCLOPENTA(C)NAPHTHO(1,2-B)FURAN-6,7(6AH)-DIONE
• 2H,6H-CYCLOPENTA(C)NAPHTHO(1,2-B)FURAN-6,7(6AH)-DIONE, 1,3,4B,10,11,11A-HEXAHYDRO-6A-HYDROXY-1,1-DIMETHYL-8-(1-METHYLETHYL)-, (4BR,6AR,9AR,11AS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9908	99.08%
Caco-2	+	0.7242	72.42%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8134	81.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8925	89.25%
OATP1B3 inhibitior	-	0.2779	27.79%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.5897	58.97%
BSEP inhibitior	-	0.5674	56.74%
P-glycoprotein inhibitior	-	0.7054	70.54%
P-glycoprotein substrate	-	0.7638	76.38%
CYP3A4 substrate	+	0.5991	59.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8742	87.42%
CYP3A4 inhibition	-	0.7147	71.47%
CYP2C9 inhibition	-	0.7067	70.67%
CYP2C19 inhibition	-	0.7897	78.97%
CYP2D6 inhibition	-	0.9373	93.73%
CYP1A2 inhibition	+	0.5470	54.70%
CYP2C8 inhibition	-	0.8008	80.08%
CYP inhibitory promiscuity	-	0.8786	87.86%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4987	49.87%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9472	94.72%
Skin irritation	+	0.5873	58.73%
Skin corrosion	-	0.9062	90.62%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5550	55.50%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.7271	72.71%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.7090	70.90%
Acute Oral Toxicity (c)	III	0.5011	50.11%
Estrogen receptor binding	+	0.7180	71.80%
Androgen receptor binding	+	0.5817	58.17%
Thyroid receptor binding	+	0.6904	69.04%
Glucocorticoid receptor binding	+	0.8169	81.69%
Aromatase binding	+	0.5812	58.12%
PPAR gamma	+	0.6008	60.08%
Honey bee toxicity	-	0.9201	92.01%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.18%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.39%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.21%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.99%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.91%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.51%	94.45%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.06%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.47%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.82%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.18%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.14%	97.14%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	82.55%	85.94%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.68%	95.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.46%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.34%	93.04%

Plants that contains it

• Amentotaxus yunnanensis
• Artemisia siversiana
• Deguelia hatschbachii
• Delphinium cyphoplectrum
• Dioscorea communis
• Euphorbia retusa
• Hemionitis artax
• Salvia przewalskii
• Stauntonia obovatifoliola
• Uvaria klaineana
• Vicia sativa

Cross-Links

• PubChem: 51002763
• NPASS: NPC106986
• LOTUS: LTS0259257
• wikiData: Q105326466