ID: ALA455372

Max Phase: Preclinical

Molecular Formula: C25H28O4

Molecular Weight: 392.50

Molecule Type: Small molecule

Representations

Synonyms (2): Erybraedin C | Erythrabyssin II
Synonyms from Alternative Forms(2):

Canonical SMILES:  CC(C)=CCc1cc2c(cc1O)OC[C@H]1c3ccc(O)c(CC=C(C)C)c3O[C@@H]21

Standard InChI:  InChI=1S/C25H28O4/c1-14(2)5-7-16-11-19-23(12-22(16)27)28-13-20-17-9-10-21(26)18(8-6-15(3)4)24(17)29-25(19)20/h5-6,9-12,20,25-27H,7-8,13H2,1-4H3/t20-,25-/m0/s1

Standard InChI Key:  LDKAMVCGTURXMH-CPJSRVTESA-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: 392.50

Molecular Weight (Monoisotopic): 392.1988

AlogP: 5.72

#Rotatable Bonds: 4

Polar Surface Area: 58.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.98

CX Basic pKa:

CX LogP: 5.82

CX LogD: 5.81

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.65

Np Likeness Score: 2.42

References

1. Taniguchi M, Kubo I..  (1993)  Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.,  56  (9): [PMID:8254349] [10.1021/np50099a012]

2. Mori-Hongo M, Takimoto H, Katagiri T, Kimura M, Ikeda Y, Miyase T..  (2009)  Melanin synthesis inhibitors from Lespedeza floribunda.,  72  (2): [PMID:19132934] [10.1021/np800395j]

3. Mori-Hongo M, Yamaguchi H, Warashina T, Miyase T..  (2009)  Melanin synthesis inhibitors from Lespedeza cyrtobotrya.,  72  (1): [PMID:19102656] [10.1021/np800535g]

4. Nguyen PH, Le TV, Thuong PT, Dao TT, Ndinteh DT, Mbafor JT, Kang KW, Oh WK..  (2009)  Cytotoxic and PTP1B inhibitory activities from Erythrina abyssinica.,  19  (23): [PMID:19836230] [10.1016/j.bmcl.2009.09.108]

5. Woo HS, Kim DW, Curtis-Long MJ, Lee BW, Lee JH, Kim JY, Kang JE, Park KH..  (2011)  Potent inhibition of bacterial neuraminidase activity by pterocarpans isolated from the roots of Lespedeza bicolor.,  21  (20): [PMID:21911291] [10.1016/j.bmcl.2011.08.046]

6. Nassief SM, Amer ME, Shawky E, Sishtla K, Mas-Claret E, Muniyandi A, Corson TW, Mulholland DA, El-Masry S..  (2023)  Antiangiogenic Pterocarpan and Flavonoid Constituents of Erythrina lysistemon.,  86  (4): [PMID:36938984] [10.1021/acs.jnatprod.2c00909]

7. Selvam C, Jordan BC, Prakash S, Mutisya D, Thilagavathi R..  (2017)  Pterocarpan scaffold: A natural lead molecule with diverse pharmacological properties.,  128  [PMID:28189086] [10.1016/j.ejmech.2017.01.023]

Source

Source(1):

• Scientific Literature