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102040-03-9 molecular structure
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(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 and InChIs

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

Cite this record

CBID:120106 http://www.chembase.cn/molecule-120106.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[39.9.3.211,14.222,25.134,38.01,46.04,9.027,32.037,42.045,53]octapentacont-44-ene-2,16,20-trione
IUPAC Traditional 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[39.9.3.211,14.222,25.134,38.01,46.04,9.027,32.037,42.045,53]octapentacont-44-ene-2,16,20-trione
tubeimoside I
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
CAS Number
102040-03-9
PubChem SID
162214459
PubChem CID
5462420

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5462420 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
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 cm3 Polarizability 126.42806 Å3
Polar Surface Area 445.19 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Pharmacology Properties Product Information Bioassay(PubChem)
Mechanism of Action
Apoptosis inducer expand Show data source
DNA synthesis inhibitor expand Show data source
Biological Source
Constit. of Bolbostemma paniculatum expand Show data source
Application(s)
Anti-inflammatory activity expand Show data source
Antitumour activity expand Show data source

DETAILS

DETAILS

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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]
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PATENTS

PATENTS

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INTERNET

INTERNET

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