ID: ALA1911631

Max Phase: Preclinical

Molecular Formula: C32H42O10

Molecular Weight: 586.68

Molecule Type: Small molecule

Representations

Synonyms (1): Yuanhuadine
Synonyms from Alternative Forms(1):

Canonical SMILES:  C=C(C)[C@@]12O[C@@]3(/C=C/C=C/CCCCC)O[C@@H]1[C@@H]1[C@@H]4O[C@]4(CO)[C@@H](O)[C@]4(O)C(=O)C(C)=C[C@H]4[C@@]1(O3)[C@H](C)[C@H]2OC(C)=O

Standard InChI:  InChI=1S/C32H42O10/c1-7-8-9-10-11-12-13-14-29-40-26-22-25-28(16-33,39-25)27(36)30(37)21(15-18(4)23(30)35)32(22,42-29)19(5)24(38-20(6)34)31(26,41-29)17(2)3/h11-15,19,21-22,24-27,33,36-37H,2,7-10,16H2,1,3-6H3/b12-11+,14-13+/t19-,21-,22+,24-,25+,26-,27-,28+,29-,30-,31+,32+/m1/s1

Standard InChI Key:  NHELFTYSELEEFD-SVAWBNMMSA-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: 586.68

Molecular Weight (Monoisotopic): 586.2778

AlogP: 2.41

#Rotatable Bonds: 9

Polar Surface Area: 144.28

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.65

CX Basic pKa:

CX LogP: 3.44

CX LogD: 3.44

Aromatic Rings: 0

Heavy Atoms: 42

QED Weighted: 0.12

Np Likeness Score: 3.77

References

1. Hong JY, Chung HJ, Lee HJ, Park HJ, Lee SK..  (2011)  Growth inhibition of human lung cancer cells via down-regulation of epidermal growth factor receptor signaling by yuanhuadine, a daphnane diterpene from Daphne genkwa.,  74  (10): [PMID:21916433] [10.1021/np2003512]

2. Li F, Sun Q, Hong L, Li L, Wu Y, Xia M, Ikejima T, Peng Y, Song S..  (2013)  Daphnane-type diterpenes with inhibitory activities against human cancer cell lines from Daphne genkwa.,  23  (9): [PMID:23558238] [10.1016/j.bmcl.2013.03.025]

3. Bang KK, Yun CY, Lee C, Jin Q, Lee JW, Jung SH, Lee D, Lee MK, Hong JT, Kim Y, Hwang BY..  (2013)  Melanogenesis inhibitory daphnane diterpenoids from the flower buds of Daphne genkwa.,  23  (11): [PMID:23623417] [10.1016/j.bmcl.2013.03.096]

4. Zhao HD, Lu Y, Yan M, Chen CH, Morris-Natschke SL, Lee KH, Chen DF..  (2020)  Rapid Recognition and Targeted Isolation of Anti-HIV Daphnane Diterpenes from Daphne genkwa Guided by UPLC-MSⁿ.,  83  (1): [PMID:31860304] [10.1021/acs.jnatprod.9b00993]

5. Pan RR, Zhang CY, Li Y, Zhang BB, Zhao L, Ye Y, Song YN, Zhang M, Tie HY, Zhang H, Zhu JY..  (2020)  Daphnane Diterpenoids from Daphne genkwa Inhibit PI3K/Akt/mTOR Signaling and Induce Cell Cycle Arrest and Apoptosis in Human Colon Cancer Cells.,  83  (4): [PMID:32223193] [10.1021/acs.jnatprod.0c00003]

6. Iyamu ID, Huang R..  (2021)  Mechanisms and inhibitors of nicotinamide N-methyltransferase.,  12  (8.0): [PMID:34458733] [10.1039/D1MD00016K]

Source

Source(1):

• Scientific Literature