2-[(5S,8R,11S,14R,17S,20S,22aR)-20-Benzyl-5-((S)-sec-butyl)-8,14-dimethyl-11-(2-methylsulfanyl-ethyl)-4,7,10,13,16,19,22-heptaoxo-icosahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosen-17-yl]-acetamide

ID: ALA456766

PubChem CID: 11115315

Max Phase: Preclinical

Molecular Formula: C35H52N8O8S

Molecular Weight: 744.92

Molecule Type: Protein

Names and Identifiers

Synonyms: Phakelli Statin 5 | Phakellistatin 5 | phakellistatin 5|phakelli statin 5|CHEMBL456766|SCHEMBL1230773

Canonical SMILES:  CC[C@H](C)[C@@H]1NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H]2CCCN2C1=O

Standard InChI:  InChI=1S/C35H52N8O8S/c1-6-19(2)28-35(51)43-15-10-13-26(43)34(50)41-24(17-22-11-8-7-9-12-22)33(49)40-25(18-27(36)44)32(48)38-20(3)29(45)39-23(14-16-52-5)31(47)37-21(4)30(46)42-28/h7-9,11-12,19-21,23-26,28H,6,10,13-18H2,1-5H3,(H2,36,44)(H,37,47)(H,38,48)(H,39,45)(H,40,49)(H,41,50)(H,42,46)/t19-,20-,21-,23-,24-,25-,26-,28-/m0/s1

Standard InChI Key:  MJIXQFVJUHBNPL-HTRACTDJSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA456766

   PHAKELLI STATIN 5

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 744.92

Molecular Weight (Monoisotopic): 744.3629

AlogP: -1.14

#Rotatable Bonds: 9

Polar Surface Area: 238.00

Molecular Species: NEUTRAL

HBA: 9

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.52

CX Basic pKa: ┄

CX LogP: -1.29

CX LogD: -1.29

Aromatic Rings: 1

Heavy Atoms: 52

QED Weighted: 0.16

Np Likeness Score: 0.79

References

1. Pettit GR, Xu J, Cichacz ZA, Williams MD, Dorsaz A, Brune DC, Boyd MR, Cerny RL.  (1994)  Antineoplastic agents 315. Isolation and structure of the marine sponge cancer cell growth inhibitor phakellistatin 5,  4  (17): [10.1016/S0960-894X(01)80108-6]

2. Pettit GR, Lippert JW, Taylor SR, Tan R, Williams MD..  (2001)  Synthesis of phakellistatin 11: a micronesia (Chuuk) marine sponge cyclooctapeptide.,  64  (7): [PMID:11473416] [10.1021/np0100441]

3. Pettit GR, Lippert JW, Taylor SR, Tan R, Williams MD..  (2001)  Synthesis of phakellistatin 11: a micronesia (Chuuk) marine sponge cyclooctapeptide.,  64  (7): [PMID:11473416] [10.1021/np0100441]

4. Ali L, Musharraf SG, Shaheen F..  (2008)  Solid-phase total synthesis of cyclic decapeptide phakellistatin 12.,  71  (6): [PMID:18489164] [10.1021/np070648q]

Source

Source(1):

• Scientific Literature