ID: ALA264610

Max Phase: Preclinical

Molecular Formula: C43H53NO6

Molecular Weight: 679.90

Molecule Type: Small molecule

Representations

Canonical SMILES:  C=C(C)[C@H]1C(=O)c2c3c(cc4c5c(n1c24)[C@@]1(C)C(CC[C@H]2[C@](C)(/C=C/C=C(\C)C(=O)O)[C@@H](O)CC[C@@]21C)C5)C1=CC(C)(C)OC(C)(C)C1[C@@H]3O

Standard InChI:  InChI=1S/C43H53NO6/c1-21(2)33-36(47)31-30-24(27-20-39(4,5)50-40(6,7)32(27)35(30)46)19-25-26-18-23-13-14-28-41(8,16-11-12-22(3)38(48)49)29(45)15-17-42(28,9)43(23,10)37(26)44(33)34(25)31/h11-12,16,19-20,23,28-29,32-33,35,45-46H,1,13-15,17-18H2,2-10H3,(H,48,49)/b16-11+,22-12+/t23?,28-,29-,32?,33-,35+,41-,42-,43+/m0/s1

Standard InChI Key:  UNCVXXVJJXJZII-AMHQYJIYSA-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: 679.90

Molecular Weight (Monoisotopic): 679.3873

AlogP: 8.18

#Rotatable Bonds: 4

Polar Surface Area: 108.99

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.47

CX Basic pKa:

CX LogP: 6.60

CX LogD: 3.72

Aromatic Rings: 2

Heavy Atoms: 50

QED Weighted: 0.17

Np Likeness Score: 3.03

References

1. Chakravarty PK, Shih TL, Colletti SL, Ayer MB, Snedden C, Kuo H, Tyagarajan S, Gregory L, Zakson-Aiken M, Shoop WL, Schmatz DM, Wyvratt M, Fisher MH, Meinke PT..  (2003)  Nodulisporic acid side-chain modifications: access to the 2", 3", 4", and 6" registers.,  13  (1): [PMID:12467636] [10.1016/s0960-894x(02)00826-0]

2. Ok D, Li C, Shih TL, Salva S, Ayer MB, Colletti SL, Chakravarty PK, Wyvratt MJ, Fisher MH, Gregory L, Zakson-Aiken M, Shoop WL, Schmatz DM, Meinke PT..  (2002)  Side-chain homologation of nodulisporic acid: synthesis of potent new dienyl derivatives.,  12  (13): [PMID:12067553] [10.1016/s0960-894x(02)00284-6]

3. Meinke PT, Ayer MB, Colletti SL, Li C, Lim J, Ok D, Salva S, Schmatz DM, Shih TL, Shoop WL, Warmke LM, Wyvratt MJ, Zakson-Aiken M, Fisher MH..  (2000)  Chemical modification of nodulisporic acid A: preliminary structure-activity relationships.,  10  (20): [PMID:11055358] [10.1016/s0960-894x(00)00469-8]

4. Ondeyka JG, Dahl-Roshak AM, Tkacz JS, Zink DL, Zakson-Aiken M, Shoop WL, Goetz MA, Singh SB..  (2002)  Nodulisporic acid B, B1, and B2: a series of 1'-deoxy-nodulisporic acids from Nodulisporium sp.,  12  (20): [PMID:12270179] [10.1016/s0960-894x(02)00621-2]

5. Meinke PT..  (2001)  Perspectives in animal health: old targets and new opportunities.,  44  (5): [PMID:11262075] [10.1021/jm990564h]

6. Ondeyka JG, Byrne K, Vesey D, Zink DL, Shoop WL, Goetz MA, Singh SB..  (2003)  Nodulisporic acids C, C1, and C2: a series of D-ring-opened nodulisporic acids from the fungus Nodulisporium sp.,  66  (1): [PMID:12542359] [10.1021/np020339u]

7. Singh SB, Ondeyka JG, Jayasuriya H, Zink DL, Ha SN, Dahl-Roshak A, Greene J, Kim JA, Smith MM, Shoop W, Tkacz JS..  (2004)  Nodulisporic acids D-F: structure, biological activities, and biogenetic relationships.,  67  (9): [PMID:15387649] [10.1021/np0498455]

Source

Source(1):

• Scientific Literature