ID: ALA218534

Max Phase: Preclinical

Molecular Formula: C23H28O8

Molecular Weight: 432.47

Molecule Type: Small molecule

Representations

Canonical SMILES:  COC(=O)C1=CC[C@@]23CC[C@@H]([C@@](C)(/C=C/C=C(\C)C(=O)O)OC2=O)[C@@]3(OC(C)=O)CC1

Standard InChI:  InChI=1S/C23H28O8/c1-14(18(25)26)6-5-10-21(3)17-9-12-22(20(28)31-21)11-7-16(19(27)29-4)8-13-23(17,22)30-15(2)24/h5-7,10,17H,8-9,11-13H2,1-4H3,(H,25,26)/b10-5+,14-6+/t17-,21+,22+,23-/m0/s1

Standard InChI Key:  VDGOFNMYZYBUDT-YDRCMHEVSA-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: 432.47

Molecular Weight (Monoisotopic): 432.1784

AlogP: 2.87

#Rotatable Bonds: 5

Polar Surface Area: 116.20

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.98

CX Basic pKa:

CX LogP: 2.95

CX LogD: -0.22

Aromatic Rings: 0

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: 3.16

References

1. Zhang H, Wang XN, Lin LP, Ding J, Yue JM..  (2007)  Indole alkaloids from three species of the Ervatamia genus: E. officinalis, E. divaricata, and E. divaricata Gouyahua.,  70  (1): [PMID:17253850] [10.1021/np060344o]

2. Liu P, Guo H, Wang W, Zhang J, Li N, Han J, Zhou J, Hu Y, Zhang T, Liu Z, Guo D..  (2007)  Cytotoxic diterpenoids from the bark of Pseudolarix kaempferi and their structure-activity relationships.,  70  (4): [PMID:17291040] [10.1021/np060439q]

3. Yin S, Wang XN, Fan CQ, Lin LP, Ding J, Yue JM..  (2007)  Limonoids from the seeds of the marine mangrove Xylocarpus granatum.,  70  (4): [PMID:17323995] [10.1021/np060632k]

4. Yang SP, Cai YJ, Zhang BL, Tong LJ, Xie H, Wu Y, Lin LP, Ding J, Yue JM..  (2008)  Structural modification of an angiogenesis inhibitor discovered from traditional Chinese medicine and a structure-activity relationship study.,  51  (1): [PMID:18078313] [10.1021/jm070906g]

5. Li XC, ElSohly HN, Nimrod AC, Clark AM..  (1999)  Two auronols from Pseudolarix amabilis.,  62  (5): [PMID:10346966] [10.1021/np980469w]

6. Li E, Clark AM, Hufford CD..  (1995)  Antifungal evaluation of pseudolaric acid B, a major constituent of Pseudolarix kaempferi.,  58  (1): [PMID:7760078] [10.1021/np50115a007]

7. Yin S, Su ZS, Zhou ZW, Dong L, Yue JM..  (2008)  Antimicrobial diterpenes from Trigonostemon chinensis.,  71  (8): [PMID:18611050] [10.1021/np800256x]

8. Gan LS, Yang SP, Fan CQ, Yue JM..  (2005)  Lignans and their degraded derivatives from Sarcostemma acidum.,  68  (2): [PMID:15730247] [10.1021/np049681s]

9. Huo J, Yang SP, Ding J, Yue JM..  (2004)  Cytotoxic sesquiterpene lactones from Eupatorium lindleyanum.,  67  (9): [PMID:15387644] [10.1021/np040023h]

10. Su ZS, Yin S, Zhou ZW, Wu Y, Ding J, Yue JM..  (2008)  Sesquiterpenoids from Hedyosmum orientale.,  71  (8): [PMID:18651771] [10.1021/np800240v]

11. He XF, Yin S, Ji YC, Su ZS, Geng MY, Yue JM..  (2010)  Sesquiterpenes and dimeric sesquiterpenoids from Sarcandra glabra.,  73  (1): [PMID:20038159] [10.1021/np9006469]

12. He XF, Wang XN, Yin S, Dong L, Yue JM..  (2011)  Ring A-seco triterpenoids with antibacterial activity from Dysoxylum hainanense.,  21  (1): [PMID:21131198] [10.1016/j.bmcl.2010.11.057]

Source

Source(1):

• Scientific Literature