IMPPAT Phytochemical information: 
Calamansanin
Calamansanin
Summary

SMILES: O=C(c1cc(O)c(c(c1)O)O)OC[C@H]1O[C@H](OC(=O)c2cc(O)c(c(c2)O)O)[C@H]2[C@H]([C@@H]1OC(=O)c1cc(O)c(c(c1c1c(O)c(O)c3c4c1c(=O)oc1c4c(c(=O)o3)cc(c1O)O)O)O)OC(=O)c1cc(O)c(c(c1-c1c(C(=O)O2)cc(O)c(c1O)O)O)O
InChI: InChI=1S/C55H34O34/c56-16-1-10(2-17(57)32(16)64)48(75)82-9-24-43(84-50(77)14-7-22(62)36(68)40(72)27(14)29-31-30-28-15(53(80)85-45(30)42(74)41(29)73)8-23(63)37(69)44(28)86-54(31)81)46-47(55(83-24)89-49(76)11-3-18(58)33(65)19(59)4-11)88-52(79)13-6-21(61)35(67)39(71)26(13)25-12(51(78)87-46)5-20(60)34(66)38(25)70/h1-8,24,43,46-47,55-74H,9H2/t24-,43-,46+,47-,55-/m1/s1
InChIKey: BPWNQDVSTSGECV-WCPWCIMFSA-N
DeepSMILES: O=CcccO)ccc6)O))O)))))OC[C@H]O[C@H]OC=O)cccO)ccc6)O))O)))))))[C@H][C@H][C@@H]6OC=O)cccO)ccc6ccO)cO)ccc6c=O)occ6cc=O)o%10))ccc6O))O)))))))))))))))O))O))))))))OC=O)cccO)ccc6-ccC=O)O%14))ccO)cc6O))O)))))))O))O
Scaffold Graph/Node/Bond level: O=C(OCC1OC(OC(=O)c2ccccc2)C2OC(=O)c3ccccc3-c3ccccc3C(=O)OC2C1OC(=O)c1ccccc1-c1ccc2oc(=O)c3cccc4oc(=O)c1c2c43)c1ccccc1
Scaffold Graph/Node level: OC(OCC1OC(OC(O)C2CCCCC2)C2OC(O)C3CCCCC3C3CCCCC3C(O)OC2C1OC(O)C1CCCCC1C1CCC2OC(O)C3CCCC4OC(O)C1C2C43)C1CCCCC1
Scaffold Graph level: CC(CCC1CC(CC(C)C2CCCCC2)C2CC(C)C3CCCCC3C3CCCCC3C(C)CC2C1CC(C)C1CCCCC1C1CCC2CC(C)C3CCCC4CC(C)C1C2C43)C1CCCCC1
Functional groups: c=O; cC(=O)OC; cC(=O)O[C@H](C)OC; cO; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Tannins
ClassyFire Subclass: Hydrolyzable tannins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenolic acids (C6-C1)
NP Classifier Class: Gallotannins
Synonymous chemical names:
calamansanin
External chemical identifiers:
CID:16174850
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Calamansanin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 1238.84
Log P RDKit 2.96
Topological polar surface area (Å2) RDKit 585.52
Number of hydrogen bond acceptors RDKit 34
Number of hydrogen bond donors RDKit 19
Number of carbon atoms RDKit 55
Number of heavy atoms RDKit 89
Number of heteroatoms RDKit 34
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 49
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.11
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 7
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 9
Total number of rings RDKit 11
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 11
Calamansanin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.0342