Deoxyshikonin

ID: ALA486627

Chembl Id: CHEMBL486627

PubChem CID: 135564821

Max Phase: Preclinical

Molecular Formula: C16H16O4

Molecular Weight: 272.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 11-Deoxyalkannin | Deoxyshikonin

Canonical SMILES:  CC(C)=CCCC1=CC(=O)c2c(O)ccc(O)c2C1=O

Standard InChI:  InChI=1S/C16H16O4/c1-9(2)4-3-5-10-8-13(19)14-11(17)6-7-12(18)15(14)16(10)20/h4,6-8,17-18H,3,5H2,1-2H3

Standard InChI Key:  VOMDIEGPEURZJO-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA486627

   DEOXYSHIKONIN

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

Calculated Properties

Molecular Weight: 272.30

Molecular Weight (Monoisotopic): 272.1049

AlogP: 3.15

#Rotatable Bonds: 3

Polar Surface Area: 74.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.52

CX Basic pKa: ┄

CX LogP: 4.24

CX LogD: 4.21

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.65

Np Likeness Score: 2.39

References

1. Honda G, Sakakibara F, Yazaki K, Tabata M..  (1988)  Isolation of deoxyshikonin, an antidermatophytic principle from Lithospermum erythrorhizon cell cultures.,  51  (1): [PMID:3373224] [10.1021/np50055a025]

2. Sevimli-Gur C, Akgun IH, Deliloglu-Gurhan I, Korkmaz KS, Bedir E..  (2010)  Cytotoxic naphthoquinones from Alkanna cappadocica ( perpendicular).,  73  (5): [PMID:20405844] [10.1021/np900778j]

3. Kim JY, Jeong HJ, Park JY, Kim YM, Park SJ, Cho JK, Park KH, Ryu YB, Lee WS..  (2012)  Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases.,  20  (5): [PMID:22300884] [10.1016/j.bmc.2012.01.011]

4. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

5. LI C, FUKUSHI Y, KAWABATA J, TAHARA S, MIZUTANI J, UYEDA I.  (1998)  Antiviral and Antifungal Activities of Some Naphthoquinones Isolated from the Roots of Lithospermum erythrorhizon,  23  (1): [10.1584/jpestics.23.54]

Source

Source(1):

• Scientific Literature