SCS-C005039
bryostatin 19
Pathway: Polyketides
Superclass: Macrolides
Class: Bryostatins
Glycoside
Chemical Structure
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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Bugula neritina
(marine bryozoan)
Kingdom
Metazoa
Phylum
Bryozoa
Class
Gymnolaemata
Order
Cheilostomatida
Family
Bugulidae
Genus
Bugula
Species
Bugula neritina
South China Sea
Records of Natural Products, 2015, 9, 271-275. || Natural Product Communications, 2013, 8, 67-68. || Chemistry of Natural Compounds, 2013, 49, 653-656. || Natural Product Communications, 2013, 8, 1069-1070. || Acta Chimica Sinica / Acta Chim. Sin, 2001. || Natural Product Communications, 2013, 8, 1127-1128. || Chemical Journal of Chinese Universities, 2007. || Acta Chimica Sinica, 2002. || Turkish Journal of Chemistry, 1999, 23(3), 339-344. || Chinese Journal of Organic Chemistry, 2002. || Chinese Journal of Chemistry, 2013, 31, 100-104. || Marine Drugs, 2068. || Helvetica Chimica Acta, 2013, 96, 1188-1196. || Liu Qing || Li Ruisheng. Study on chemical constituents of Chinese soft coral. (37) Structure of a novel polyhydroxylated steroid / 《() --》. || The Journal of Antibiotics, 2013, 66, 327-331. || Indian Journal of Chemistry, Section B, 2002. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 2002. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 1999. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 1998, 37(3), 82-85. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 1987. || Chinese Journal of Organic Chemistry, 2007. || Natural Product Communications, 2015, 10, 1033-1037. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 2001. || Chemical Research in Chinese Universities, 1998, 14(4), 426-427. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 1986. || Phytochemistry Letters, 2013, 6, 392-396. || Natural Product Reports, 1997. || Chinese Journal of Organic Chemistry, 2001. || Journal of Natural Products, 2013. || Chinese Journal of Marine Drugs, 1998, 17(1), 1-3. || Chemical Journal of Chinese Universities, 2021. || Chinese Journal of Marine Drugs, 2003, 22, 28-30. || Natural Product Communications, 2015, 10, 1203-1208. || Archives of Pharmacal Research, 2013, 36, 739-744. || Steroids, 2013, 78, 396-400.
Drug-likeness (Lipinski Ro5)
Molecular Weight
879.0 Da
Threshold ≤ 500
ALogP
3.56
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
17
Threshold ≤ 10
2 violations (MW, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C45H66O17
Molecular Weight:
879.0060 Da
SMILES:
CCCC(=O)O[C@H]1C2=CC(=O)O[C@@H]2[C@H]2C[C@H]([C@@H](C)O)OC(=O)C[C@H](O)C[C@@H]3C[C@H](OC(=O)C(C)(C)C)C(C)(C)[C@](O)(C[C@@H]4C/C(=C/C(=O)OC)C[C@H](/C=C/C(C)(C)[C@]1(O)O2)O4)O3
InChIKey:
WUELAQMKFWZEMC-GKGNCSQSSA-N
InChI:
InChI=1S/C45H66O17/c1-11-12-34(48)60-39-30-21-37(51)59-38(30)32-22-31(24(2)46)57-36(50)19-26(47)18-28-20-33(58-40(52)41(3,4)5)43(8,9)44(53,61-28)23-29-16-25(17-35(49)55-10)15-27(56-29)13-14-42(6,7)45(39,54)62-32/h13-14,17,21,24,26-29,31-33,38-39,46-47,53-54H,11-12,15-16,18-20,22-23H2,1-10H3/b14-13+,25-17+/t24-,26-,27+,28-,29+,31-,32-,33+,38+,39+,44+,45-/m1/s1
Calculated Properties
ALogP:
3.556 lipophilicity
TPSA:
240.11 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
17
Rotatable Bonds:
6
Ring Count:
5
(0 aromatic)
Chiral Centers:
12
Fsp³:
0.7556 fraction sp³ carbon
Database Information
Compound ID:
SCS-C005039
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Macrolides
NPClassifier Class:
Bryostatins
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.