alterperylenol

ID: ALA1081908

PubChem CID: 14213481

Max Phase: Preclinical

Molecular Formula: C20H14O6

Molecular Weight: 350.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Alterperylenol | CHEMBL1081908

Canonical SMILES:  O=C1C[C@@H](O)[C@H]2c3c(ccc(O)c31)-c1ccc(O)c3c1[C@]2(O)C=CC3=O

Standard InChI:  InChI=1S/C20H14O6/c21-10-3-1-8-9-2-4-11(22)17-12(23)5-6-20(26,18(9)17)19-14(25)7-13(24)16(10)15(8)19/h1-6,14,19,21-22,25-26H,7H2/t14-,19+,20-/m1/s1

Standard InChI Key:  MTOHOIPTYJIUCH-VOBQZIQPSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
    2.4751   -6.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740   -7.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1880   -7.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862   -5.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1897   -8.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4743   -8.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4737   -9.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1878   -9.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009   -6.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9043   -7.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6187   -7.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3344   -7.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3310   -6.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -5.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6210   -8.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066   -8.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9068   -9.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6198   -9.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3343   -9.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3357   -8.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1837   -4.9861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6074   -4.9757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895  -10.7552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6189  -10.7496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0492   -7.4508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6118   -6.6305    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3319   -7.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 15 16  1  0
  6  7  1  0
  1  2  2  0
  7  8  2  0
  8 17  1  0
 16  5  1  0
  3  5  1  0
 15 20  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 11 15  1  0
  9 10  1  0
  4 21  1  0
  9  4  2  0
 14 22  2  0
  4  1  1  0
  8 23  1  0
 18 24  2  0
  2  3  1  0
 12 25  1  1
  5  6  2  0
 11 26  1  1
  3 10  2  0
 15 27  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1081908

   ALTERPERYLENOL

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

Calculated Properties

Molecular Weight: 350.33

Molecular Weight (Monoisotopic): 350.0790

AlogP: 1.75

#Rotatable Bonds: ┄

Polar Surface Area: 115.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.27

CX Basic pKa: ┄

CX LogP: 2.03

CX LogD: 1.98

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.58

Np Likeness Score: 2.28

References

1. Kjer J, Wray V, Edrada-Ebel R, Ebel R, Pretsch A, Lin W, Proksch P..  (2009)  Xanalteric acids I and II and related phenolic compounds from an endophytic Alternaria sp. isolated from the mangrove plant Sonneratia alba.,  72  (11): [PMID:19835393] [10.1021/np900417g]

2. Chen JL, Sperry J, Ip NY, Brimble MA.  (2011)  Natural products targeting telomere maintenance,  2  (4): [10.1039/C0MD00241K]

Source

Source(1):

• Scientific Literature