ID: ALA396609

Max Phase: Preclinical

Molecular Formula: C28H40O6

Molecular Weight: 472.62

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(C)C[C@@H](c1c(O)c(C=O)c(O)c(C=O)c1O)[C@@]1(C)CC[C@@H]2[C@@H]1[C@H]1[C@@H](CC[C@@]2(C)O)C1(C)C

Standard InChI:  InChI=1S/C28H40O6/c1-14(2)11-19(20-24(32)15(12-29)23(31)16(13-30)25(20)33)27(5)9-7-18-22(27)21-17(26(21,3)4)8-10-28(18,6)34/h12-14,17-19,21-22,31-34H,7-11H2,1-6H3/t17-,18-,19+,21-,22-,27-,28-/m1/s1

Standard InChI Key:  IBLPTYJTKWQCDX-MOTAWSDJSA-N

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

Properties

Molecular Weight: 472.62

Molecular Weight (Monoisotopic): 472.2825

AlogP: 5.41

#Rotatable Bonds: 6

Polar Surface Area: 115.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.68

CX Basic pKa:

CX LogP: 7.63

CX LogD: 6.72

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.41

Np Likeness Score: 1.86

References

1. Yang XW, Guo QM, Wang Y, Xu W, Tian L, Tian XJ..  (2007)  Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.,  17  (4): [PMID:17118653] [10.1016/j.bmcl.2006.11.021]

2. Osawa K, Yasuda H, Morita H, Takeya K, Itokawa H..  (1996)  Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus.,  59  (9): [PMID:8864235] [10.1021/np9604994]

3. Yang SP, Zhang XW, Ai J, Gan LS, Xu JB, Wang Y, Su ZS, Wang L, Ding J, Geng MY, Yue JM..  (2012)  Potent HGF/c-Met axis inhibitors from Eucalyptus globulus: the coupling of phloroglucinol and sesquiterpenoid is essential for the activity.,  55  (18): [PMID:22934600] [10.1021/jm3007454]

4. Yu Y, Gan LS, Yang SP, Sheng L, Liu QF, Chen SN, Li J, Yue JM..  (2016)  Eucarobustols A-I, Conjugates of Sesquiterpenoids and Acylphloroglucinols from Eucalyptus robusta.,  79  (5): [PMID:27142786] [10.1021/acs.jnatprod.6b00090]

5. Qin XJ, Jin LY, Yu Q, Liu H, Khan A, Yan H, Hao XJ, An LK, Liu HY..  (2018)  Eucalypglobulusals A-J, Formyl-Phloroglucinol-Terpene Meroterpenoids from Eucalyptus globulus Fruits.,  81  (12): [PMID:30543429] [10.1021/acs.jnatprod.8b00430]

6. Pham TA, Hu XL, Huang XJ, Ma MX, Feng JH, Li JY, Hou JQ, Zhang PL, Nguyen VH, Nguyen MT, Xiong F, Fan CL, Zhang XQ, Ye WC, Wang H..  (2019)  Phloroglucinols with Immunosuppressive Activities from the Fruits of Eucalyptus globulus.,  82  (4): [PMID:30848923] [10.1021/acs.jnatprod.8b00920]

Source

Source(1):

• Scientific Literature