(1S,7S,10S,13S,19S,22S,25S,28S)-22,25,28-tris[(2S)-butan-2-yl]-10-[(4-hydroxyphenyl)methyl]-13-(propan-2-yl)-3,9,12,15,21,24,27,30-octaazatetracyclo[28.3.0.03,7.015,19]tritriacontan-2,8,11,14,20,23,26,29-octone

• ChemBase ID: 155634
• Molecular Formular: C47H72N8O9
• Molecular Mass: 893.12278
• Monoisotopic Mass: 892.54222592
• SMILES: CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N1)C(C)C)Cc1ccc(cc1)O)[C@@H](C)CC)[C@@H](C)CC
• Canonical SMILES: CC[C@@H]([C@@H]1NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@H]2N(C(=O)[C@H]3N(C(=O)[C@@H](NC(=O)[C@@H](NC1=O)[C@H](CC)C)[C@H](CC)C)CCC3)CCC2)C(C)C)C
• InChI: InChI=1S/C47H72N8O9/c1-9-27(6)37-43(60)51-38(28(7)10-2)44(61)52-39(29(8)11-3)47(64)55-24-14-17-35(55)45(62)53-22-12-15-33(53)41(58)48-32(25-30-18-20-31(56)21-19-30)40(57)49-36(26(4)5)46(63)54-23-13-16-34(54)42(59)50-37/h18-21,26-29,32-39,56H,9-17,22-25H2,1-8H3,(H,48,58)(H,49,57)(H,50,59)(H,51,60)(H,52,61)/t27-,28-,29-,32-,33-,34-,35-,36-,37-,38-,39-/m0/s1
• InChIKey: GEELDTSKBDMDCJ-GDLJMZEHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,7S,10S,13S,19S,22S,25S,28S)-22,25,28-tris[(2S)-butan-2-yl]-10-[(4-hydroxyphenyl)methyl]-13-(propan-2-yl)-3,9,12,15,21,24,27,30-octaazatetracyclo[28.3.0.0^3,^7.0^1^5,^1^9]tritriacontan-2,8,11,14,20,23,26,29-octone
• IUPAC Traditional name: (1S,7S,10S,13S,19S,22S,25S,28S)-22,25,28-tris[(2S)-butan-2-yl]-10-[(4-hydroxyphenyl)methyl]-13-isopropyl-3,9,12,15,21,24,27,30-octaazatetracyclo[28.3.0.0^3,^7.0^1^5,^1^9]tritriacontan-2,8,11,14,20,23,26,29-octone
• Synonyms: HS-1; Hymenistatin I

Database IDs

• MDL Number: MFCD00909204
• PubChem SID: 162249772
• PubChem CID: 71312177

CALCULATED PROPERTIES

• Acid pKa: 9.500751
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): 2.7622497
• LogD (pH = 7.4): 2.7588851
• Log P: 2.7622926
• Molar Refractivity: 237.8318 cm^3
• Polarizability: 93.296616 Å^3
• Polar Surface Area: 226.66 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: >99% (HPLC)
• Empirical Formula (Hill Notation): C47H72N8O9

DETAILS

Sigma Aldrich - H8409

Amino Acid Sequence
Pro-Pro-Tyr-Val-Pro-Leu-Ile-Ile
Biochem/physiol Actions
Exerts an immunosuppressive effect on humoral and cellular immune responses similar to cyclosporin A.