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2D Structure
Also known as: 58316-41-9, Saikosaponinb2, (2s,3r,4s,5s,6r)-2-[(2r,3r,4s,5s,6r)-2-[[(3s,4r,4ar,6ar,6bs,8r,8as,14ar,14bs)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy]-3,5-dihydroxy-6-methyloxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol, Schembl7523565, Chembl3792981, Chebi:183954
Molecular Formula
C42H68O13
Molecular Weight
781.0  g/mol
InChI Key
WRYJYFCCMSVEPQ-ORAXXRKOSA-N

(2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5S,6R)-2-{[(3S,4R,4aR,6aR,6bS,8R,8aS,14aR,14bS)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is a natural product found in Bupleurum falcatum with data available.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(3S,4R,4aR,6aR,6bS,8R,8aS,14aR,14bS)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy]-3,5-dihydroxy-6-methyloxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
2.1.2 InChI
InChI=1S/C42H68O13/c1-21-29(47)34(55-35-32(50)31(49)30(48)24(18-43)53-35)33(51)36(52-21)54-28-11-12-38(4)25(39(28,5)19-44)10-13-40(6)26(38)9-8-22-23-16-37(2,3)14-15-42(23,20-45)27(46)17-41(22,40)7/h8-9,21,24-36,43-51H,10-20H2,1-7H3/t21-,24-,25-,26-,27-,28+,29+,30-,31+,32-,33-,34+,35+,36+,38+,39+,40-,41-,42-/m1/s1
2.1.3 InChI Key
WRYJYFCCMSVEPQ-ORAXXRKOSA-N
2.1.4 Canonical SMILES
CC1C(C(C(C(O1)OC2CCC3(C(C2(C)CO)CCC4(C3C=CC5=C6CC(CCC6(C(CC54C)O)CO)(C)C)C)C)O)OC7C(C(C(C(O7)CO)O)O)O)O
2.1.5 Isomeric SMILES
C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@H]([C@]2(C)CO)CC[C@@]4([C@@H]3C=CC5=C6CC(CC[C@@]6([C@@H](C[C@]54C)O)CO)(C)C)C)C)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Saikosaponin A

2. Saikosaponin B

3. Saikosaponin B1

4. Saikosaponin B3

5. Saikosaponin B4

6. Saikosaponin C

7. Saikosaponin D

8. Saikosaponin K

9. Saikosaponin L

10. Saikosaponins

2.2.2 Depositor-Supplied Synonyms

1. 58316-41-9

2. Saikosaponinb2

3. (2s,3r,4s,5s,6r)-2-[(2r,3r,4s,5s,6r)-2-[[(3s,4r,4ar,6ar,6bs,8r,8as,14ar,14bs)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy]-3,5-dihydroxy-6-methyloxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

4. Schembl7523565

5. Chembl3792981

6. Chebi:183954

7. Hy-n0248

8. S9303

9. Zinc85643336

10. Akos037514824

11. Ccg-270463

12. Cs-0008279

13. 316s419

14. A869478

15. Q-100669

16. Q63395661

17. (3b,4a,16a)-16,23,28-trihydroxyoleana-11,13(18)-dien-3-yl-6-deoxy-3-o-beta-d-glucopyranosyl-beta-d-galactopyranoside

2.3 Create Date
2007-12-05
3 Chemical and Physical Properties
Molecular Weight 781.0 g/mol
Molecular Formula C42H68O13
XLogP32.5
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count13
Rotatable Bond Count7
Exact Mass780.46599222 g/mol
Monoisotopic Mass780.46599222 g/mol
Topological Polar Surface Area219 Ų
Heavy Atom Count55
Formal Charge0
Complexity1500
Isotope Atom Count0
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)


Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)


Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)


Immunosuppressive Agents

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)