RC-552

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C102H193N2O21P
Molecular Weight	1814.5984
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 13
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)N[C@H]1[C@H](OC[C@H]2OC(O)[C@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)[C@@H](O)[C@@H]2O)O[C@H](CO)[C@@H](OP(O)(O)=O)[C@@H]1OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC

InChI

InChIKey=JWBXGVSYUHYUJY-MOYMLGNLSA-N

InChI=1S/C102H193N2O21P/c1-7-13-19-25-31-37-40-42-43-45-48-54-60-65-71-77-92(109)120-85(74-68-62-56-50-35-29-23-17-11-5)80-90(107)104-96-100(124-94(111)81-86(75-69-63-57-51-36-30-24-18-12-6)121-93(110)78-72-66-58-52-46-39-33-27-21-15-9-3)99(125-126(115,116)117)87(82-105)123-102(96)118-83-88-97(112)98(113)95(101(114)122-88)103-89(106)79-84(73-67-61-55-49-34-28-22-16-10-4)119-91(108)76-70-64-59-53-47-44-41-38-32-26-20-14-8-2/h84-88,95-102,105,112-114H,7-83H2,1-6H3,(H,103,106)(H,104,107)(H2,115,116,117)/t84-,85-,86-,87-,88-,95-,96-,97-,98-,99-,100-,101?,102-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C102H193N2O21P
Molecular Weight	1814.5984
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	12 / 13
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:08:57 GMT 2025` Edited by `admin` on `Mon Mar 31 23:08:57 GMT 2025`
Record UNII	C51W8V7996
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RC 552

Preferred Name

English

RC-552

Common Name

English

RC-552C

Code

English

((1R)-1-(2-(((2R,3R,4R,5S,6R)-2-(((2R,3S,4R,5R)-5-(((3R)-3-HEXADECANOYLOXYTETRADECANOYL)AMINO)-3,4,6-TRIHYDROXY-TETRAHYDROPYRAN-2-YL)METHOXY)-6-(HYDROXYMETHYL)-5-PHOSPHONOOXY-4-((3R)-3-TETRADECANOYLOXYTETRADECANOYL)OXY-TETRAHYDROPYRAN-3-YL)AMINO)-2-OXO-E

Systematic Name

English

D-GLUCOSE, 2-DEOXY-6-O-(2-DEOXY-2-(((3R)-1-OXO-3-((1-OXOOCTADECYL)OXY)TETRADECYL)AMINO)-3-O-((3R)-1-OXO-3-((1-OXOTETRADECYL)OXY)TETRADECYL)-4-O-PHOSPHONO-.BETA.-D-GLUCOPYRANOSYL)-2-(((3R)-1-OXO-3-((1-OXOHEXADECYL)OXY)TETRADECYL)AMINO)-

Systematic Name

English

Code System Code Type Description

CAS

253119-91-4

Created by admin on Mon Mar 31 23:08:57 GMT 2025 , Edited by admin on Mon Mar 31 23:08:57 GMT 2025

PRIMARY

PUBCHEM

9833899

Created by admin on Mon Mar 31 23:08:57 GMT 2025 , Edited by admin on Mon Mar 31 23:08:57 GMT 2025

PRIMARY

FDA UNII

C51W8V7996

Created by admin on Mon Mar 31 23:08:57 GMT 2025 , Edited by admin on Mon Mar 31 23:08:57 GMT 2025

PRIMARY

Related Record Type Details


					C51W8V7996

RC-552

ACTIVE MOIETY

Comments:

Mechanism of Action: Nitric oxide synthase stimulants, Highest Development Phase: Discontinued for Ischaemic heart disorders and Reperfusion injury


					C51W8V7996

RC-552

ACTIVE MOIETY

Comments:

In contrast with monophosphoryl lipid A (MLA), which has also been reported to be cardioprotective at similar doses in dogs, RC-552 was approximately 100 times less prone to cause fever in the USP rabbit pyrogen test. Likewise, RC-552 did not induce secretion of the proinflammatory cytokines TNF, IL-6 or IL-8 from THP-1 cells or alter the expression of adhesion molecules on human neutrophils at concentrations up to 10 microg/ml.