ID: ALA397309

Max Phase: Preclinical

Molecular Formula: C21H24O7

Molecular Weight: 388.42

Molecule Type: Small molecule

Representations

Synonyms (2): 3'-Hydroxyisovalerylshikonin | Beta-Hydroxyisovalerylshikonin
Synonyms from Alternative Forms(2):

Canonical SMILES:  CC(C)=CC[C@@H](OC(=O)CC(C)(C)O)C1=CC(=O)c2c(O)ccc(O)c2C1=O

Standard InChI:  InChI=1S/C21H24O7/c1-11(2)5-8-16(28-17(25)10-21(3,4)27)12-9-15(24)18-13(22)6-7-14(23)19(18)20(12)26/h5-7,9,16,22-23,27H,8,10H2,1-4H3/t16-/m1/s1

Standard InChI Key:  MXANJRGHSFELEJ-MRXNPFEDSA-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: 388.42

Molecular Weight (Monoisotopic): 388.1522

AlogP: 2.83

#Rotatable Bonds: 6

Polar Surface Area: 121.13

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.50

CX Basic pKa:

CX LogP: 3.57

CX LogD: 3.54

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.39

Np Likeness Score: 2.19

References

1. An S, Park YD, Paik YK, Jeong TS, Lee WS..  (2007)  Human ACAT inhibitory effects of shikonin derivatives from Lithospermum erythrorhizon.,  17  (4): [PMID:17157006] [10.1016/j.bmcl.2006.11.024]

2. Cui XR, Tsukada M, Suzuki N, Shimamura T, Gao L, Koyanagi J, Komada F, Saito S..  (2008)  Comparison of the cytotoxic activities of naturally occurring hydroxyanthraquinones and hydroxynaphthoquinones.,  43  (6): [PMID:17949858] [10.1016/j.ejmech.2007.08.009]

3. Rao Z, Liu X, Zhou W, Yi J, Li SS..  (2011)  Synthesis and antitumour activity of β-hydroxyisovalerylshikonin analogues.,  46  (9): [PMID:21689869] [10.1016/j.ejmech.2011.05.065]

4. 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]

5. Kretschmer N, Rinner B, Deutsch AJ, Lohberger B, Knausz H, Kunert O, Blunder M, Boechzelt H, Schaider H, Bauer R..  (2012)  Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.,  75  (5): [PMID:22530779] [10.1021/np2006499]

6. 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