Molecule

Holyrine A

AlkaPlorer ID: AK006675

Synonym: None

IUPAC Name: 3-[(2R,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4,6,8,10,15,17,19,21-nonaen-12-one

Structure

SMILES: C[C@@H]1O[C@@H](N2C3=CC=CC=C3C3=C2C2=C(C4=C3C(O)=NC4)C3=CC=CC=C3N2)C[C@@H](N)[C@H]1O

InChI: InChI=1S/C26H24N4O3/c1-12-25(31)16(27)10-19(33-12)30-18-9-5-3-7-14(18)21-22-15(11-28-26(22)32)20-13-6-2-4-8-17(13)29-23(20)24(21)30/h2-9,12,16,19,25,29,31H,10-11,27H2,1H3,(H,28,32)/t12-,16+,19+,25-/m0/s1

InChIKey: QNQXRLNOOGRQEB-FUJFFIKUSA-N

Reference

Cytochrome P450 Homolog Is Responsible for C–N Bond Formation between Aglycone and Deoxysugar in the Staurosporine Biosynthesis of<i>Streptomyces</i>sp. TP-A0274

PubChem CID: 10503251

LOTUS: LTS0254290

{

NPAtlas: NPA010381

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Actinomyces sp.	Actinomyces	Actinomycetaceae	Actinomycetales	Actinomycetes	Actinomycetota	None	Bacteria

Properties Information

Molecule Weight: 440.5030000000001

TPSA？: 108.79

MolLogP？: 4.242800000000004

Number of H-Donors: 4

Number of H-Acceptors: 5

RingCount: 7

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	HCT-116	IC50	5100.0	nM	10.1021/acs.jnatprod.8b00103
Homo sapiens	K562	IC50	7700.0	nM	10.1021/acs.jnatprod.8b00103
Homo sapiens	L02	IC50	5800.0	nM	10.1021/acs.jnatprod.8b00103
Homo sapiens	Protein kinase C theta	IC50	260.0	nM	10.1021/acs.jmedchem.0c01271
Homo sapiens	Protein kinase C theta	Inhibition	50.0	%	10.1021/acs.jmedchem.0c01271
None	Unchecked	IC50	7000.0	nM	10.1021/acs.jnatprod.8b00103

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT013086	C[C@@H]1O[C@@H](n2c3ccccc3c3c4c(c5c6ccccc6[nH]c5c32)CNC4=O)C[C@@H](N)[C@H]1O>>CC1(O)O[C@@H](n2c3ccccc3c3c4c(c5c6ccccc6[nH]c5c32)CNC4=O)C[C@@H](N)[C@H]1O	RXN-10932
AKRT013087	C[C@@H]1O[C@@H](n2c3ccccc3c3c4c(c5c6ccccc6[nH]c5c32)CNC4=O)C[C@@H](N)[C@H]1O>>C[C@]12O[C@H](C[C@@H](N)[C@H]1O)n1c3ccccc3c3c4c(c5c6ccccc6n2c5c31)CNC4=O	R11123
AKRT015180	Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O[C@@H]3C[C@@H](N)[C@@H](O)[C@H](C)O3)O2)c(=O)[nH]c1=O.O=C1NCc2c1c1c3ccccc3[nH]c1c1[nH]c3ccccc3c21>>C[C@@H]1O[C@@H](n2c3ccccc3c3c4c(c5c6ccccc6[nH]c5c32)CNC4=O)C[C@@H](N)[C@H]1O	RXN-10931