ID: ALA524100

Max Phase: Preclinical

Molecular Formula: C21H26O5

Molecular Weight: 358.43

Molecule Type: Small molecule

Representations

Synonyms (1): Malabaricone C
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C(CCCCCCCCc1ccc(O)c(O)c1)c1c(O)cccc1O

Standard InChI:  InChI=1S/C21H26O5/c22-16-13-12-15(14-20(16)26)8-5-3-1-2-4-6-9-17(23)21-18(24)10-7-11-19(21)25/h7,10-14,22,24-26H,1-6,8-9H2

Standard InChI Key:  HCOZRFYGIFMIEX-UHFFFAOYSA-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: 358.43

Molecular Weight (Monoisotopic): 358.1780

AlogP: 4.67

#Rotatable Bonds: 10

Polar Surface Area: 97.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.86

CX Basic pKa:

CX LogP: 6.56

CX LogD: 6.55

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.28

Np Likeness Score: 0.67

References

1. Orabi KY, Mossa JS, el-Feraly FS..  (1991)  Isolation and characterization of two antimicrobial agents from mace (Myristica fragrans).,  54  (3): [PMID:1955885] [10.1021/np50075a017]

2. Patro BS, Tyagi M, Saha J, Chattopadhyay S..  (2010)  Comparative nuclease and anti-cancer properties of the naturally occurring malabaricones.,  18  (19): [PMID:20805034] [10.1016/j.bmc.2010.08.011]

3. Cuong TD, Hung TM, Na M, Ha do T, Kim JC, Lee D, Ryoo S, Lee JH, Choi JS, Min BS..  (2011)  Inhibitory effect on NO production of phenolic compounds from Myristica fragrans.,  21  (22): [PMID:21978676] [10.1016/j.bmcl.2011.09.021]

4. Chong YM, Yin WF, Ho CY, Mustafa MR, Hadi AH, Awang K, Narrima P, Koh CL, Appleton DR, Chan KG..  (2011)  Malabaricone C from Myristica cinnamomea exhibits anti-quorum sensing activity.,  74  (10): [PMID:21910441] [10.1021/np100872k]

5. Abdul Wahab SM, Sivasothy Y, Liew SY, Litaudon M, Mohamad J, Awang K..  (2016)  Natural cholinesterase inhibitors from Myristica cinnamomea King.,  26  (15): [PMID:27236720] [10.1016/j.bmcl.2016.05.046]

6. Park JY, Hwan Lim S, Ram Kim B, Jae Jeong H, Kwon HJ, Song GY, Bae Ryu Y, Song Lee W..  (2017)  Sialidase inhibitory activity of diarylnonanoid and neolignan compounds extracted from the seeds of Myristica fragrans.,  27  (14): [PMID:28551100] [10.1016/j.bmcl.2017.05.055]

7. Prabha B, Neethu S, Krishnan SL, Sherin DR, Madhukrishnan M, Ananthakrishnan R, Rameshkumar KB, Manojkumar TK, Jayamurthy P, Radhakrishnan KV..  (2018)  Antidiabetic potential of phytochemicals isolated from the stem bark of Myristica fatua Houtt. var. magnifica (Bedd.) Sinclair.,  26  (12): [PMID:29789207] [10.1016/j.bmc.2018.05.020]

8. Othman MA, Yuyama K, Murai Y, Igarashi Y, Mikami D, Sivasothy Y, Awang K, Monde K..  (2019)  Malabaricone C as Natural Sphingomyelin Synthase Inhibitor against Diet-Induced Obesity and Its Lipid Metabolism in Mice.,  10  (8): [PMID:31413799] [10.1021/acsmedchemlett.9b00171]

Source

Source(1):

• Scientific Literature