Basic information
- CAS
6834-98-6- Standard SMILES
CCCCCC(O)C1C(=O)OC(C)C(O)/C=C/C=C/C=C/C=C/C=C(\C)C(O)C(O)C(O)CC(O)CC(O)CC(O)CC(O)CC1O- InChIKey
AGJUUQSLGVCRQA-DBHIOOTNSA-N- Molecular formula
- C35H58O12
- Average molar mass
- 670.8 g/mol
- Monoisotopic mass
- 670.39282728
Names & identifiers
- Preferred name
- Oxacyclooctacosa-17,21,23,25-pentaen-2-one, 4,6,8,10,12,14,15,16,27-nonahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-
- IUPAC
- (17E,19E,21E,23E,25E)-4,6,8,10,12,14,15,16,27-nonahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
- English name
- Fungichromin
- Molecular formula
- C35H58O12
- Molecular weight
- 670.83
Names & synonyms
NSC105388NSC276732NSC277813WLN: T-28-OV RU TU VU A&U C&UTJ CYQ5 DQ FQ HQ JQ LQ NQ OQ PQ R1 E&Q F&1Pentaene antibioticOxacyclooctacosa-17,21,23,25-pentaen-2-one, 4,6,8,10,12,14,15,16,27-nonahydroxy-3-(1-hydroxyhexyl)-17,28-dimethyl-S 232FCRC-21SCHEMBL153509CHEMBL1993028HY-N14746NSC-277813
Show more names
LagosinCogomycinFungichrominLagosin【antibiotic】(3R,4S,6S,8S,10R,12R,14R,15R,16R,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,15,16,27-nonahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-oneOxacyclooctacosa-17,19,21,23,25-pentaen-2-one, 4,6,8,10,12,14,15,16,27-nonahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-, (3R,4S,6S,8S,10R,12R,14R,15R,16R,17E,19E,21E,23E,25E,27S,28R)-
TN10324NS00011777
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 229 Ų
- Hydrogen bond donors
- 10
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 5
- Heavy atoms
- 47
- Formal charge
- 0
- Complexity
- 1,020
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Melting point
- 157 · 157-162° (dec)
- alpha
- 20 · D20 -227.7° (c = 0.53 in DMF)
- Boiling point
- 914 · 914.0±65.0 °C(Predicted)
- Density
- 1.196 · 1.196±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in DMSO
- form
- solid
- pka
- 12.77 · 12.77±0.70(Predicted)
- color
- Light yellow to yellow
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 JB340D58S · 1JB340D58S
- Toxicity
- 50 in · LD50 in mice (mg/kg): 1624 orally; 33.3 i.p. (Umezawa, Tanaka)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LD50 in mice (mg/kg): 1624 orally; 33.3 i.p. (Umezawa, Tanaka)
Chemistry & industry
Applications
UsesLagosin is a pentaene antifungal produced by Streptomyces, first isolated in 1958 by researchers at MIT in the USA. The discovery was soon followed by several independent isolations as lagosin and cogomyin. Initially these metabolites were thought to be isomeric, but Pandey and colleagues at NCI definitively demonstrated they were identical. Structurally, lagosin is 14-hydroxyfilipin III and the most polar member of the filipin family of fungicides. Lagosin exhibits broad spectrum antifungal and antitumor activity and, like filipin, acts via interaction with cell membrane sterols.
Suppliers24 total
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
Aladdin Scientific[email protected]
孟成科技（上海）有限公司400-820-6829 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
上海皓之翔生物科技有限公司（原上海拓青化工有限公司）526763801 13301653310 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
上海德加源生物科技有限公司18301711315 18301711315 · [email protected]
Related reactions
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Compound notes
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