U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C28H42O6
Molecular Weight 474.6295
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 3
Charge 0

SHOW SMILES / InChI
Structure of AMBRUTICIN

SMILES

CC[C@H]1O[C@H](CC=C1C)C(\C)=C\[C@H](C)\C=C\[C@H]2[C@@H](C)[C@@H]2\C=C\[C@@H]3O[C@H](CC(O)=O)C[C@H](O)[C@H]3O

InChI

InChIKey=TYIXBSJXUFTELJ-LQJOTGEPSA-N
InChI=1S/C28H42O6/c1-6-24-17(3)8-11-25(34-24)18(4)13-16(2)7-9-21-19(5)22(21)10-12-26-28(32)23(29)14-20(33-26)15-27(30)31/h7-10,12-13,16,19-26,28-29,32H,6,11,14-15H2,1-5H3,(H,30,31)/b9-7+,12-10+,18-13+/t16-,19-,20+,21+,22+,23+,24-,25-,26+,28-/m1/s1

HIDE SMILES / InChI

Molecular Formula C28H42O6
Molecular Weight 474.6295
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 3
Optical Activity UNSPECIFIED

Ambruticin is a natural polyketide isolated from the myxobacteria Sorangium cellulosum. Ambruticin possesses antifungal activity and works by interfering with the osmoregulatory system by activating fungal high osmolarity glycerol (HOG) pathway. This results in an accumulation of intracellular glycerol, which in turn causes water influx and swelling of the cell. This ultimately leads to cellular leakage and cell death. Although ambruticin appeared to be the only oral agent capable of eliciting a high order of biological cure against experimental coccidioidomycosis, research support was discontinued in 1977 because this antibiotic had limited activity against Candida albicans.

Approval Year

Substance Class Chemical
Created
by admin
on Sat Dec 16 15:57:29 GMT 2023
Edited
by admin
on Sat Dec 16 15:57:29 GMT 2023
Record UNII
X794618736
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMBRUTICIN
INN   USAN  
USAN   INN  
Official Name English
6-[2-[2-[5-(6-Ethyl-3,6-dihydro-5-methyl-2H-pyran-2-yl)-3-methyl-1,4-hexadienyl]-3-methylcyclopropyl]vinyl]tetrahydro-4,5-dihydroxy-2H-pyran-2-acetic acid
Systematic Name English
SMP-78 ACID S
Code English
2H-PYRAN-2-ACETIC ACID, 6-(2-(2-(5-(6-ETHYL-3,6-DIHYDRO-5-METHYL-2H-PYRAN-2-YL)-3-METHYL-1,4-HEXADIENYL)-3-METHYLCYCLOPROPYL)ETHENYL)TETRAHYDRO-4,5-DIHYDROXY-
Common Name English
W7783
Code English
ambruticin [INN]
Common Name English
W-7783
Code English
(+)-AMBRUTICIN
Common Name English
NSC-328415
Code English
AMBRUTICIN [USAN]
Common Name English
(+)-AMBRUTICIN S
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Sat Dec 16 15:57:29 GMT 2023 , Edited by admin on Sat Dec 16 15:57:29 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID701024202
Created by admin on Sat Dec 16 15:57:29 GMT 2023 , Edited by admin on Sat Dec 16 15:57:29 GMT 2023
PRIMARY
EVMPD
SUB05398MIG
Created by admin on Sat Dec 16 15:57:29 GMT 2023 , Edited by admin on Sat Dec 16 15:57:29 GMT 2023
PRIMARY
FDA UNII
X794618736
Created by admin on Sat Dec 16 15:57:29 GMT 2023 , Edited by admin on Sat Dec 16 15:57:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL522783
Created by admin on Sat Dec 16 15:57:29 GMT 2023 , Edited by admin on Sat Dec 16 15:57:29 GMT 2023
PRIMARY
SMS_ID
100000087668
Created by admin on Sat Dec 16 15:57:29 GMT 2023 , Edited by admin on Sat Dec 16 15:57:29 GMT 2023
PRIMARY
INN
4456
Created by admin on Sat Dec 16 15:57:29 GMT 2023 , Edited by admin on Sat Dec 16 15:57:29 GMT 2023
PRIMARY
NSC
328415
Created by admin on Sat Dec 16 15:57:29 GMT 2023 , Edited by admin on Sat Dec 16 15:57:29 GMT 2023
PRIMARY
CAS
58857-02-6
Created by admin on Sat Dec 16 15:57:29 GMT 2023 , Edited by admin on Sat Dec 16 15:57:29 GMT 2023
PRIMARY
NCI_THESAURUS
C75987
Created by admin on Sat Dec 16 15:57:29 GMT 2023 , Edited by admin on Sat Dec 16 15:57:29 GMT 2023
PRIMARY
PUBCHEM
6918547
Created by admin on Sat Dec 16 15:57:29 GMT 2023 , Edited by admin on Sat Dec 16 15:57:29 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY