18-Hydroxylabda-8(17),13(E)-dien-15-oic acid

ID: ALA4217347

PubChem CID: 15558527

Max Phase: Preclinical

Molecular Formula: C20H32O3

Molecular Weight: 320.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@H]2[C@](C)(CO)CCC[C@]2(C)[C@H]1CC/C(C)=C/C(=O)O

Standard InChI:  InChI=1S/C20H32O3/c1-14(12-18(22)23)6-8-16-15(2)7-9-17-19(3,13-21)10-5-11-20(16,17)4/h12,16-17,21H,2,5-11,13H2,1,3-4H3,(H,22,23)/b14-12+/t16-,17-,19-,20+/m0/s1

Standard InChI Key:  YGILXMANNHJYJZ-GQSMEJGBSA-N

Molfile:  

     RDKit          2D

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   10.1116   -9.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7012   -8.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2904   -9.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9964   -7.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9964   -7.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7049   -6.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4175   -7.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4185   -7.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1302   -8.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8453   -7.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8442   -7.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1281   -6.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4102   -6.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4143   -8.7684    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1259   -5.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8398   -5.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5560   -5.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2619   -5.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5581   -6.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9804   -5.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9874   -6.6946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6878   -5.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6948   -9.7848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6655   -7.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3  2  1  0
  4  5  1  0
  4  6  1  0
  5  2  1  0
  2  8  1  0
  7  6  1  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  7 13  1  1
  8 14  1  6
 12 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
  1 23  1  0
 11 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4217347

   (E)-5-[(1S,4aR,5R,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid

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: 320.47

Molecular Weight (Monoisotopic): 320.2351

AlogP: 4.57

#Rotatable Bonds: 5

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.62

CX Basic pKa: ┄

CX LogP: 4.20

CX LogD: 1.49

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: 3.05

References

1. Kuo PC, Hung HY, Nian CW, Hwang TL, Cheng JC, Kuo DH, Lee EJ, Tai SH, Wu TS..  (2017)  Chemical Constituents and Anti-inflammatory Principles from the Fruits of Forsythia suspensa.,  80  (4): [PMID:28218000] [10.1021/acs.jnatprod.6b01141]

Source

Source(1):

• Scientific Literature