ID: ALA402194

Max Phase: Preclinical

Molecular Formula: C30H38O4

Molecular Weight: 462.63

Molecule Type: Small molecule

Representations

Canonical SMILES:  C/C(=C\C=C\C(C)=C1\C(=O)C[C@H]2[C@@]3(C)CCC(=O)C(C)(C)[C@@H]3CC[C@]12C)c1ccc(C)c(=O)o1

Standard InChI:  InChI=1S/C30H38O4/c1-18(22-12-11-20(3)27(33)34-22)9-8-10-19(2)26-21(31)17-24-29(6)16-14-25(32)28(4,5)23(29)13-15-30(24,26)7/h8-12,23-24H,13-17H2,1-7H3/b10-8+,18-9+,26-19-/t23-,24-,29-,30-/m0/s1

Standard InChI Key:  CXOJYPVZDPNKAI-WJBIETBOSA-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: 462.63

Molecular Weight (Monoisotopic): 462.2770

AlogP: 6.62

#Rotatable Bonds: 3

Polar Surface Area: 64.35

Molecular Species: NEUTRAL

HBA: 4

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 6.17

CX LogD: 6.17

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.37

Np Likeness Score: 2.68

References

1. Pettit GR, Hogan F, Xu JP, Tan R, Nogawa T, Cichacz Z, Pettit RK, Du J, Ye QH, Cragg GM, Herald CL, Hoard MS, Goswami A, Searcy J, Tackett L, Doubek DL, Williams L, Hooper JN, Schmidt JM, Chapuis JC, Tackett DN, Craciunescu F..  (2008)  Antineoplastic agents. 536. New sources of naturally occurring cancer cell growth inhibitors from marine organisms, terrestrial plants, and microorganisms(1a,).,  71  (3): [PMID:18327911] [10.1021/np700738k]

2. Su JY, Meng YH, Zeng LM, Fu X, Schmitz FJ..  (1994)  Stellettin A, a new triterpenoid pigment from the marine sponge Stelletta tenuis.,  57  (10): [PMID:7807129] [10.1021/np50112a017]

3. Tabudravu JN, Jaspars M..  (2001)  Stelliferin riboside, a triterpene monosaccharide isolated from the Fijian sponge Geodia globostellifera.,  64  (6): [PMID:11421753] [10.1021/np010019v]

4. Lv F, Deng Z, Li J, Fu H, van Soest RW, Proksch P, Lin W..  (2004)  Isomalabaricane-type compounds from the marine sponge Rhabdastrella aff. distincta.,  67  (12): [PMID:15620246] [10.1021/np040145+]

5. Liu WK, Cheung FW, Che CT..  (2006)  Stellettin A induces oxidative stress and apoptosis in HL-60 human leukemia and LNCaP prostate cancer cell lines.,  69  (6): [PMID:16792413] [10.1021/np058122y]

6. Tasdemir D, Mangalindan GC, Concepción GP, Verbitski SM, Rabindran S, Miranda M, Greenstein M, Hooper JN, Harper MK, Ireland CM..  (2002)  Bioactive isomalabaricane triterpenes from the marine sponge Rhabdastrella globostellata.,  65  (2): [PMID:11858759] [10.1021/np0104020]

7. Liu WK, Ling YH, Cheung FW, Che CT..  (2012)  Stellettin A induces endoplasmic reticulum stress in murine B16 melanoma cells.,  75  (4): [PMID:22439644] [10.1021/np2008158]

8. Chen B, Qiu P, Xu B, Zhao Q, Gu YC, Fu L, Bi S, Lan L, Wang CY, Guo YW..  (2022)  Cytotoxic and Antibacterial Isomalabaricane Terpenoids from the Sponge Rhabdastrella globostellata.,  85  (7.0): [PMID:35767002] [10.1021/acs.jnatprod.2c00348]

Source

Source(1):

• Scientific Literature