Mitraphylline

Details

• Internal ID: e1fcd5ae-435c-4f2c-b469-4a89911eb3b8
• Taxonomy: Organoheterocyclic compounds > Indolizidines
• IUPAC Name: methyl (1S,4aS,5aS,6R,10aR)-1-methyl-2'-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-carboxylate
• SMILES (Canonical): CC1C2CN3CCC4(C3CC2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O
• SMILES (Isomeric): C[C@H]1[C@H]2CN3CC[C@]4([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O
• InChI: InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21+/m0/s1
• InChI Key: JMIAZDVHNCCPDM-DAFCLMLCSA-N
• Popularity: 24 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄N₂O₄
• Molecular Weight: 368.40 g/mol
• Exact Mass: 368.17360725 g/mol
• Topological Polar Surface Area (TPSA): 67.90 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.06
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 509-80-8
• Mitraphilline
• Mitraphyllin
• Rubradinine
• Ajmalicine oxindole B
• Rubradinin
• UNII-1H9SRL2456
• 1H9SRL2456
• EINECS 208-106-0
• Methyl 19alpha-methyl-2-oxoformosanan-16-carboxylate
• CHEBI:6957
• DTXSID50198926
• Methyl (19alpha)-19-methyl-2-oxoformosanan-16-carboxylate
• SPIRO(3H-INDOLE-3,6'(4'AH)-(1H)PYRANO(3,4-F)INDOLIZINE)-4'-CARBOXYLIC ACID, 1,2,5',5'A,7',8',10',10'A-OCTAHYDRO-1'-METHYL-2-OXO-, METHYL ESTER, (1'S,3R,4'AS,5'AS,10'AR)-
• methyl (1S,4aS,5aS,6R,10aR)-1-methyl-2'-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-carboxylate
• MLS000728610
• SEC-BUTYLMETHYLSULFIDE
• CHEMBL2135897
• DTXCID10121417
• Formosanan-16-carboxylic acid, 19-methyl-2-oxo-, methyl ester, (19.alpha.)-
• HMS2267P09
• HY-N6946
• CCG-36401
• NSC717700
• AKOS040760558
• NSC-717700
• MS-25901
• SMR000470795
• CS-0081397
• C09227
• E87144
• MITRAPHYLLINE (CONSTITUENT OF CAT'S CLAW)
• Q10859059
• MITRAPHYLLINE (CONSTITUENT OF CAT'S CLAW) [DSC]
• Formosanan-16-carboxylic acid, 19-methyl-2-oxo-, methyl ester, (19alpha)-
• (1'S,3R,4a'S,5a'S,10a'R)-methyl 1'-methyl-2-oxo-1',4a',5',5a',7',8',10',10a'-octahydrospiro[indoline-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9598	95.98%
Caco-2	+	0.7013	70.13%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5603	56.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8774	87.74%
OATP1B3 inhibitior	+	0.9244	92.44%
MATE1 inhibitior	-	0.7209	72.09%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6857	68.57%
P-glycoprotein inhibitior	+	0.6545	65.45%
P-glycoprotein substrate	+	0.5986	59.86%
CYP3A4 substrate	+	0.7189	71.89%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	-	0.7556	75.56%
CYP3A4 inhibition	-	0.7361	73.61%
CYP2C9 inhibition	-	0.7119	71.19%
CYP2C19 inhibition	-	0.8184	81.84%
CYP2D6 inhibition	-	0.8491	84.91%
CYP1A2 inhibition	-	0.6693	66.93%
CYP2C8 inhibition	+	0.5951	59.51%
CYP inhibitory promiscuity	-	0.8626	86.26%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5848	58.48%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9967	99.67%
Skin irritation	-	0.7821	78.21%
Skin corrosion	-	0.9360	93.60%
Ames mutagenesis	-	0.6344	63.44%
Human Ether-a-go-go-Related Gene inhibition	+	0.8732	87.32%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.5781	57.81%
skin sensitisation	-	0.8611	86.11%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.6693	66.93%
Acute Oral Toxicity (c)	III	0.6045	60.45%
Estrogen receptor binding	+	0.7753	77.53%
Androgen receptor binding	+	0.7205	72.05%
Thyroid receptor binding	-	0.5083	50.83%
Glucocorticoid receptor binding	+	0.5567	55.67%
Aromatase binding	-	0.5965	59.65%
PPAR gamma	+	0.5356	53.56%
Honey bee toxicity	-	0.8146	81.46%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9754	97.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.72%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.64%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.65%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.91%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.35%	99.23%
CHEMBL4208	P20618	Proteasome component C5	88.04%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.92%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.32%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.21%	93.03%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.96%	90.71%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.47%	94.08%
CHEMBL5028	O14672	ADAM10	85.16%	97.50%
CHEMBL2581	P07339	Cathepsin D	84.88%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.50%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.09%	97.14%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.54%	100.00%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	80.15%	91.65%

Plants that contains it

• Ageratina tomentella
• Capsicum annuum
• Caralluma stalagmifera
• Catharanthus roseus
• Drymaria cordata
• Euthamia graminifolia
• Ficus nervosa
• Mitragyna hirsuta
• Mitragyna parvifolia
• Prosopis cineraria
• Rauvolfia caffra
• Rubus xanthocarpus
• Rumex chalepensis
• Uncaria attenuata
• Uncaria elliptica
• Uncaria gambir
• Uncaria guianensis
• Uncaria hirsuta
• Uncaria tomentosa

Cross-Links

• PubChem: 94160
• NPASS: NPC298851
• LOTUS: LTS0042883
• wikiData: Q10859059