(1S,4S,7S,8S,9R,11S,13S,14S,18S,22S,25S,27R,28S,29S,30R,32R,34R,35S,37R,38R,41R,42R,46S,53S,54R,55R,56R,57S,58R)-7,8,18,28,29,35,55,56,58-nonahydroxy-30,54-bis(hydroxymethyl)-13,18,37,41,48,48,53,54-octamethyl-57-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,5,10,12,15,21,24,26,31,33-decaoxadecacyclo[39.9.3.211,14.222,25.134,38.01,46.04,9.027,32.037,42.045,53]octapentacont-44-ene-2,16,20-trione

• ChemBase ID: 120106
• Molecular Formular: C63H98O29
• Molecular Mass: 1319.43482
• Monoisotopic Mass: 1318.61937712
• SMILES: [C@@]12([C@@H]3[C@@]([C@@H](O[C@H]4[C@H](O[C@H]5[C@@H]([C@H]([C@@H](OC(=O)C[C@@](CC(=O)O[C@@H]6[C@H]([C@H]([C@H](O[C@H]7[C@H](OC(=O)[C@]89[C@H](C%10=CC[C@H]1[C@]([C@@]%10(CC8)C)(CC3)C)CC(CC9)(C)C)OC[C@@H]([C@@H]7O)O)O[C@H]6C)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)(O)C)CO5)O)O)[C@H]([C@@H]([C@H](O4)CO)O)O)[C@H](C2)O)(CO)C)C
• Canonical SMILES: OC[C@H]1O[C@H]2O[C@H]3[C@@H](O)C[C@]4([C@H]([C@]3(C)CO)CC[C@@]3([C@@H]4CC=C4[C@@]3(C)CC[C@@]3([C@H]4CC(C)(C)CC3)C(=O)O[C@@H]3OC[C@@H]([C@@H]([C@H]3O[C@@H]3O[C@H]([C@H](OC(=O)C[C@@](CC(=O)O[C@H]4CO[C@@H](O[C@@H]2[C@H]([C@@H]1O)O)[C@H](O)[C@H]4O)(C)O)[C@@H](O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)[C@H]3O)C)O)O)C)C
• InChI: InChI=1S/C63H98O29/c1-26-46-47(88-51-43(76)38(71)30(67)22-81-51)45(78)53(84-26)90-48-39(72)31(68)23-82-54(48)92-56(79)63-15-13-57(2,3)17-28(63)27-9-10-35-59(5)18-29(66)50(60(6,25-65)34(59)11-12-62(35,8)61(27,7)14-16-63)91-55-49(42(75)40(73)32(21-64)86-55)89-52-44(77)41(74)33(24-83-52)85-36(69)19-58(4,80)20-37(70)87-46/h9,26,28-35,38-55,64-68,71-78,80H,10-25H2,1-8H3/t26-,28-,29-,30+,31-,32+,33-,34?,35+,38-,39-,40+,41-,42-,43+,44+,45+,46-,47-,48+,49+,50-,51-,52-,53-,54-,55-,58-,59-,60-,61+,62+,63-/m0/s1
• InChIKey: MCPFEAJYKIXPQF-WOUIMHRJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,7S,8S,9R,11S,13S,14S,18S,22S,25S,27R,28S,29S,30R,32R,34R,35S,37R,38R,41R,42R,46S,53S,54R,55R,56R,57S,58R)-7,8,18,28,29,35,55,56,58-nonahydroxy-30,54-bis(hydroxymethyl)-13,18,37,41,48,48,53,54-octamethyl-57-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,5,10,12,15,21,24,26,31,33-decaoxadecacyclo[39.9.3.2^1^1,^1^4.2^2^2,^2^5.1^3^4,^3^8.0^1,^4^6.0^4,^9.0^2^7,^3^2.0^3^7,^4^2.0^4^5,^5^3]octapentacont-44-ene-2,16,20-trione
• IUPAC Traditional name: tubeimoside I; (1S,4S,7S,8S,9R,11S,13S,14S,18S,22S,25S,27R,28S,29S,30R,32R,34R,35S,37R,38R,41R,42R,46S,53S,54R,55R,56R,57S,58R)-7,8,18,28,29,35,55,56,58-nonahydroxy-30,54-bis(hydroxymethyl)-13,18,37,41,48,48,53,54-octamethyl-57-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,5,10,12,15,21,24,26,31,33-decaoxadecacyclo[39.9.3.2^1^1,^1^4.2^2^2,^2^5.1^3^4,^3^8.0^1,^4^6.0^4,^9.0^2^7,^3^2.0^3^7,^4^2.0^4^5,^5^3]octapentacont-44-ene-2,16,20-trione
• Synonyms: (1S,4S,7S,8S,9R,11S,13S,14S,18S,22S,25S,27R,28S,29S,30R,32R,34R,35S,37R,38R,41R,42R,46S,53S,54R,55R,56R,57S,58R)-7,8,18,28,29,35,55,56,58-nonahydroxy-30,54-bis(hydroxymethyl)-13,18,37,41,48,48,53,54-o ctamethyl-57-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl] oxy}-3,5,10,12,15,21,24,26,31,33-decaoxadecacyclo[39.9.3.2^{11,14}.2^{22,25}.1^{34,38}.0^{1,46}.0^{4,9}.0^{27,32}.0^{37,42}.0^{45,53}]octapentacont-44-ene-2,16,20-trione; Tubeimoside 1; Tubeimoside A

Database IDs

• CAS Number: 102040-03-9
• PubChem SID: 162214459
• PubChem CID: 5462420

CALCULATED PROPERTIES

• Acid pKa: 11.747
• H Acceptors: 26
• H Donor: 14
• LogD (pH = 5.5): -1.5936364
• LogD (pH = 7.4): -1.5936557
• Log P: -1.5936362
• Molar Refractivity: 306.5672 cm^3
• Polarizability: 126.42806 Å^3
• Polar Surface Area: 445.19 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Apoptosis inducer; DNA synthesis inhibitor

Product Information

• Biological Source: Constit. of Bolbostemma paniculatum
• Application(s): Anti-inflammatory activity; Antitumour activity

REFERENCES

• 1. Yu L, Ma R, Wang Y, Nishino H. Potent anti-tumor activity and low toxicity of tubeimoside 1 isolated from Bolbostemma paniculatum. Planta Med. 1994 Jun;60(3):204-8.
• 2. Yu TX, Ma RD, Yu LJ. Structure-activity relationship of tubeimosides in anti-inflammatory, antitumor, and antitumor-promoting effects. Acta Pharmacol Sin. 2001 May;22(5):463-8.
• 3. Weng XY, Ma RD, Yu LJ. [Apoptosis of human nasopharyngeal carcinoma CNE-2Z cells induced by tubeimoside I] Ai Zheng. 2003 Aug;22(8):806-11. [Article in Chinese]