ID: ALA510103

Max Phase: Preclinical

Molecular Formula: C35H36N4O5

Molecular Weight: 592.70

Molecule Type: Small molecule

Representations

Canonical SMILES:  C=Cc1c(C)c2cc3nc(c4c5[nH]c(cc6nc(cc1[nH]2)C(C)=C6CC)c(C)c5C(=O)[C@@H]4C(=O)OC)[C@@H](CCC(=O)O)[C@@H]3C

Standard InChI:  InChI=1S/C35H36N4O5/c1-8-19-15(3)22-12-24-17(5)21(10-11-28(40)41)32(38-24)30-31(35(43)44-7)34(42)29-18(6)25(39-33(29)30)14-27-20(9-2)16(4)23(37-27)13-26(19)36-22/h8,12-14,17,21,31,36,39H,1,9-11H2,2-7H3,(H,40,41)/b22-12-,23-13-,24-12-,25-14-,26-13-,27-14-,32-30-/t17-,21-,31+/m0/s1

Standard InChI Key:  NSFSLUUZQIAOOX-QEWKCGBTSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 592.70

Molecular Weight (Monoisotopic): 592.2686

AlogP: 7.12

#Rotatable Bonds: 6

Polar Surface Area: 138.03

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.61

CX Basic pKa: 5.01

CX LogP: 5.52

CX LogD: 3.78

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.20

Np Likeness Score: 1.45

References

1. Cheng HH, Wang HK, Ito J, Bastow KF, Tachibana Y, Nakanishi Y, Xu Z, Luo TY, Lee KH..  (2001)  Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C. cyrtophyllum.,  64  (7): [PMID:11473423] [10.1021/np000595b]

2. Zhang HJ, Tan GT, Hoang VD, Hung NV, Cuong NM, Soejarto DD, Pezzuto JM, Fong HH..  (2003)  Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea.,  66  (2): [PMID:12608862] [10.1021/np020379y]

3. You H, Yoon HE, Yoon JH, Ko H, Kim YC..  (2011)  Synthesis of pheophorbide-a conjugates with anticancer drugs as potential cancer diagnostic and therapeutic agents.,  19  (18): [PMID:21873067] [10.1016/j.bmc.2011.07.058]

4. Pan W, Liu K, Guan Y, Tan GT, Hung NV, Cuong NM, Soejarto DD, Pezzuto JM, Fong HH, Zhang H..  (2014)  Bioactive compounds from Vitex leptobotrys.,  77  (3): [PMID:24404757] [10.1021/np400779v]

5. Kurihara H, Kagawa Y, Konno R, Kim SM, Takahashi K..  (2014)  Lipoxygenase inhibitors derived from marine macroalgae.,  24  (5): [PMID:24495846] [10.1016/j.bmcl.2014.01.046]

6. Krapf MK, Gallus J, Vahdati S, Wiese M..  (2018)  New Inhibitors of Breast Cancer Resistance Protein (ABCG2) Containing a 2,4-Disubstituted Pyridopyrimidine Scaffold.,  61  (8): [PMID:29547272] [10.1021/acs.jmedchem.7b01012]

7. Silbermann K,Li J,Namasivayam V,Baltes F,Bendas G,Stefan SM,Wiese M.  (2020)  Superior Pyrimidine Derivatives as Selective ABCG2 Inhibitors and Broad-Spectrum ABCB1, ABCC1, and ABCG2 Antagonists.,  63  (18): [PMID:32787102] [10.1021/acs.jmedchem.0c00961]

Source

Source(1):

• Scientific Literature