(-)-pinoresinol

ID: ALA460862

Chembl Id: CHEMBL460862

PubChem CID: 12309637

Max Phase: Preclinical

Molecular Formula: C20H22O6

Molecular Weight: 358.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (-)-Pinoresinol | CHEMBL460862|BDBM50292291

Canonical SMILES:  COc1cc([C@@H]2OC[C@H]3[C@@H]2CO[C@H]3c2ccc(O)c(OC)c2)ccc1O

Standard InChI:  InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19-,20-/m0/s1

Standard InChI Key:  HGXBRUKMWQGOIE-FEBSWUBLSA-N

Alternative Forms

1. Parent:

   

   ALA460862

   (-)-PINORESINOL

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: 358.39

Molecular Weight (Monoisotopic): 358.1416

AlogP: 3.19

#Rotatable Bonds: 4

Polar Surface Area: 77.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.61

CX Basic pKa:

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.87

Np Likeness Score: 1.00

References

1. Deng S, Palu 'K, West BJ, Su CX, Zhou BN, Jensen JC..  (2007)  Lipoxygenase inhibitory constituents of the fruits of noni (Morinda citrifolia) collected in Tahiti.,  70  (5): [PMID:17378609] [10.1021/np0605539]

2. Zhang HJ, Tamez PA, Vu DH, Ghee TT, Nguyen VH, Le TX, Le MH, Nguyen MC, Do TT, Soejarto DD, Fong HH, Pezzuto JM..  (2001)  Antimalarial compounds from Rhaphidophora decursiva.,  64  (6): [PMID:11421741] [10.1021/np010037c]

3. Liang S, Shen YH, Tian JM, Wu ZJ, Jin HZ, Zhang WD, Yan SK..  (2008)  Phenylpropanoids from Daphne feddei and their inhibitory activities against NO production.,  71  (11): [PMID:18986199] [10.1021/np8004166]

4. Kim KH, Moon E, Choi SU, Kim SY, Lee KR..  (2011)  Biological evaluation of phenolic constituents from the trunk of Berberis koreana.,  21  (8): [PMID:21420296] [10.1016/j.bmcl.2011.02.104]

5. Li Y, Cheng W, Zhu C, Yao C, Xiong L, Tian Y, Wang S, Lin S, Hu J, Yang Y, Guo Y, Yang Y, Li Y, Yuan Y, Chen N, Shi J..  (2011)  Bioactive neolignans and lignans from the bark of Machilus robusta.,  74  (6): [PMID:21627109] [10.1021/np2001896]

6. Cutillo F, D'Abrosca B, DellaGreca M, Fiorentino A, Zarrelli A..  (2003)  Lignans and neolignans from Brassica fruticulosa: effects on seed germination and plant growth.,  51  (21): [PMID:14518939] [10.1021/jf034644c]

7. Nguyen PH, Yang JL, Uddin MN, Park SL, Lim SI, Jung DW, Williams DR, Oh WK..  (2013)  Protein tyrosine phosphatase 1B (PTP1B) inhibitors from Morinda citrifolia (Noni) and their insulin mimetic activity.,  76  (11): [PMID:24224843] [10.1021/np400533h]

Source

Source(1):

• Scientific Literature