Molecule

Rhynchophylline

AlkaPlorer ID: AK003523

Synonym: None

IUPAC Name: methyl (E)-2-[(3R,6'R,7'S,8'aS)-6'-ethyl-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate

Structure

SMILES: CC[C@H]1CN2CC[C@]3(C(O)=NC4=C3C=CC=C4)[C@@H]2C[C@@H]1/C(=C\OC)C(=O)OC

InChI: InChI=1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22+/m0/s1

InChIKey: DAXYUDFNWXHGBE-KAXDATADSA-N

Reference

New heteroyohimbine-type oxindole alkaloid from the leaves of Thai Mitragyna hirsuta

PubChem CID: 5281408

CAS: 76-66-4

LOTUS: LTS0269766

SuperNatural Ⅲ: SN0060888-09

NPASS: NPC63210

data_source: manually

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Uncaria macrophylla	Uncaria	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Uncaria rhynchophylla	Uncaria	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Uncaria sinensis	Uncaria	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 384.4760000000002

TPSA？: 71.36

MolLogP？: 3.349700000000002

Number of H-Donors: 1

Number of H-Acceptors: 5

RingCount: 4

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	Angiotensin-converting enzyme	Inhibition	10.03	%	10.1016/j.bmcl.2017.07.016
Homo sapiens	HERG	Activity	-16.0	mV	10.1021/np800729q
Homo sapiens	HERG	Activity	30.0	ms	10.1021/np800729q
Homo sapiens	HERG	IC50	773000.0	nM	10.1021/np800729q
Homo sapiens	HL-60	IC50	40000.0	nM	10.1021/np1004938
Homo sapiens	Serotonin 1a (5-HT1a) receptor	EC50	17.42	ug.mL-1	10.1016/j.bmc.2021.116270
Homo sapiens	Serotonin 1a (5-HT1a) receptor	EC50	10300.0	nM	10.1021/acs.jnatprod.9b00532
Homo sapiens	SW480	IC50	40000.0	nM	10.1021/np1004938
Homo sapiens	Voltage-gated potassium channel subunit Kv1.2	Activity	19.4	None	10.1021/np800729q
Rattus norvegicus	Aorta	IC50	30.0	ug.mL-1	10.1021/np1004938
None	ADMET	Drug metabolism	22.0	%	10.1016/j.bmc.2021.116270
None	ADMET	F	25.9	%	10.1016/j.bmc.2021.116270
None	NON-PROTEIN TARGET	Activity	nan	None	10.1021/np8000305
None	Unchecked	Activity	-34.6	mV	10.1021/np800729q
None	Unchecked	Activity	-6.5	mV	10.1021/np800729q
None	Unchecked	Activity	3.7	None	10.1021/np800729q
None	Unchecked	Activity	7.7	mV	10.1021/np800729q
None	Unchecked	Activity	11.8	None	10.1021/np800729q
None	Unchecked	Activity	23.2	None	10.1021/np800729q
None	Unchecked	Activity	35.0	ms	10.1021/np800729q
None	Unchecked	Activity	60.8	ms	10.1021/np800729q
None	Unchecked	Activity	72.5	%	10.1021/np800729q
None	Unchecked	Activity	77.0	%	10.1016/j.ejmech.2022.114566
None	Unchecked	Activity	93.3	ms	10.1021/np800729q
None	Unchecked	Activity	98.0	%	10.1021/np800729q
None	Unchecked	Activity	115.0	%	10.1021/np800729q
None	Unchecked	Activity	1607.0	ms	10.1021/np800729q
None	Unchecked	Activity	1905.0	ms	10.1021/np800729q
None	Unchecked	Activity	nan	None	10.1021/np800729q
None	Unchecked	IC50	7900.0	nM	10.1021/np800729q
None	Unchecked	IC50	18500.0	nM	10.1021/np8000305
None	Unchecked	Inhibition	32.0	%	10.1021/np8000305
None	Unchecked	Inhibition	35.9	%	10.1021/np8000305
None	Unchecked	Inhibition	37.6	%	10.1016/j.ejmech.2022.114566
None	Unchecked	Inhibition	75.8	%	10.1021/np8000305
None	Unchecked	Inhibition	106.5	%	10.1021/np8000305