3-aminomethylrifamycin SV

ID: ALA3274602

Chembl Id: CHEMBL3274602

PubChem CID: 90678781

Max Phase: Preclinical

Molecular Formula: C38H50N2O12

Molecular Weight: 726.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(c(CN)c(O)c4c3C2=O)NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C

Standard InChI:  InChI=1S/C38H50N2O12/c1-16-11-10-12-17(2)37(48)40-28-23(15-39)32(45)25-26(33(28)46)31(44)21(6)35-27(25)36(47)38(8,52-35)50-14-13-24(49-9)18(3)34(51-22(7)41)20(5)30(43)19(4)29(16)42/h10-14,16,18-20,24,29-30,34,42-46H,15,39H2,1-9H3,(H,40,48)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,24-,29-,30+,34+,38-/m0/s1

Standard InChI Key:  ZBJJYWIEVGRTPN-UPZFVJMDSA-N

Alternative Forms

1. Parent:

   

   ALA3274602

   [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-(aminomethyl)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate

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

Calculated Properties

Molecular Weight: 726.82

Molecular Weight (Monoisotopic): 726.3364

AlogP: 4.21

#Rotatable Bonds: 3

Polar Surface Area: 227.33

Molecular Species: BASE

HBA: 13

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 6.94

CX Basic pKa: 8.84

CX LogP: 2.20

CX LogD: 2.26

Aromatic Rings: 2

Heavy Atoms: 52

QED Weighted: 0.13

Np Likeness Score: 2.17

References

1. McCarthy JR, Moore JL, Wysong DV..  (1977)  3-N-Substituted aminomethyl derivatives of rifamycin SV. A convenient method of synthesis, cyclization of certain derivatives, and anticellular and antiviral activities of several derivatives.,  20  (10): [PMID:198544] [10.1021/jm00220a009]

Source

Source(1):

• Scientific Literature