ID: ALA539920

Max Phase: Preclinical

Molecular Formula: C27H30N2O9

Molecular Weight: 526.54

Molecule Type: Small molecule

Representations

Canonical SMILES:  COC1=C(C)C(=O)C2=C(C1=O)[C@@H]1[C@@H]3CC4=C(C(=O)C(OC)=C(C)C4=O)[C@H](COC(C)=O)N3[C@@H](O)[C@H](C2)N1C

Standard InChI:  InChI=1S/C27H30N2O9/c1-10-21(31)13-7-15-20-19-14(22(32)11(2)26(37-6)24(19)34)8-16(28(20)4)27(35)29(15)17(9-38-12(3)30)18(13)23(33)25(10)36-5/h15-17,20,27,35H,7-9H2,1-6H3/t15-,16-,17-,20-,27-/m0/s1

Standard InChI Key:  QCUVHQFXYHRYHX-PIHYCAAOSA-N

Molecule Features

Natural Product: Yes

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: 526.54

Molecular Weight (Monoisotopic): 526.1951

AlogP: 0.13

#Rotatable Bonds: 4

Polar Surface Area: 139.75

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.96

CX Basic pKa: 4.07

CX LogP: 0.80

CX LogD: 0.80

Aromatic Rings: 0

Heavy Atoms: 38

QED Weighted: 0.40

Np Likeness Score: 1.80

References

1. Lane JW, Estevez A, Mortara K, Callan O, Spencer JR, Williams RM..  (2006)  Antitumor activity of tetrahydroisoquinoline analogues 3-epi-jorumycin and 3-epi-renieramycin G.,  16  (12): [PMID:16632360] [10.1016/j.bmcl.2006.03.042]

2. Charupant K, Daikuhara N, Saito E, Amnuoypol S, Suwanborirux K, Owa T, Saito N..  (2009)  Chemistry of renieramycins. Part 8: synthesis and cytotoxicity evaluation of renieramycin M-jorunnamycin A analogues.,  17  (13): [PMID:19457672] [10.1016/j.bmc.2009.05.009]

3. Fang Y, Li H, Ji B, Cheng K, Wu B, Li Z, Zheng C, Hua H, Li D..  (2021)  Renieramycin-type alkaloids from marine-derived organisms: Synthetic chemistry, biological activity and structural modification.,  210  [PMID:33333398] [10.1016/j.ejmech.2020.113092]

Source

Source(1):

• Scientific Literature