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72496-41-4

Basic Information
CAS No.: 72496-41-4
Name: 5,12-Naphthacenedione,10-[[3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-a-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-,(8S,10S)-
Article Data: 1
Cas Database
Molecular Structure:
Molecular Structure of 72496-41-4 (5,12-Naphthacenedione,10-[[3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-a-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-,(8S,10S)-)
Formula: C32H37NO12
Molecular Weight: 627.645
Synonyms: 5,12-Naphthacenedione,10-[[3-amino-2,3,6-trideoxy-4-O-(tetrahydro-2H-pyran-2-yl)-a-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-,[8S-[8a,10a(S*)]]-;5,12-Naphthacenedione,10-[[3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-a-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-,(8S,10S)- (9CI);(2''R)-4'-O-Tetrahydropyranyladriamycin;(2''R)-4'-O-Tetrahydropyranyldoxorubicin;4'-O-Tetrahydropyranyladriamycin;Pinorubicin;Pirarubicin;THP-Adriamycin;Therarubicin;
EINECS: N/A
Density: 1.519 g/cm3
Melting Point: 188-192 °C (dec.)
Boiling Point: 834.659 °C at 760 mmHg
Flash Point: 458.586 °C
Solubility: Soluble in water and methanol, slightly soluble in alcohol, chloroform, insoluble in are hexane and ethyl ether
Appearance: Red crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information: N/A
PSA: 204.30000
LogP: 2.25250
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Specification

The Pirarubicin, with the CAS registry number 72496-41-4, is also known as 4'-O-Tetrahydropyranyladriamycin. It belongs to the product categories of Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C32H37NO12 and molecular weight is 627.64. What's more, its systematic name is (8S,10S)-10-((3-Amino-2,3,6-trideoxy-4-O-(2R-tetrahydro-2H-pyran-2-yl)-α-L-lyxo-hexopyranosyl)oxy)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione. Its classification codes are: (1)Antineoplastic Agents; (2)Drug / Therapeutic Agent; (3)Mutation data. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides. Its storage temperature is 2 - 8°C. It can be prepared by doxorubicin and dihydropyran, and it is an anthracycline-based anti-tumor antibiotic.

Physical properties of Pirarubicin are: (1)ACD/LogP: 3.852; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 1.15; (4)ACD/LogD (pH 7.4): 2.30; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 14.08; (7)ACD/KOC (pH 5.5): 5.83; (8)ACD/KOC (pH 7.4): 83.87; (9)#H bond acceptors: 13; (10)#H bond donors: 6; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 204.3 Å2; (13)Index of Refraction: 1.67; (14)Molar Refractivity: 154.56 cm3; (15)Molar Volume: 413.309 cm3; (16)Polarizability: 61.272×10-24cm3; (17)Surface Tension: 82.99 dyne/cm; (18)Density: 1.519 g/cm3; (19)Flash Point: 458.586 °C; (20)Enthalpy of Vaporization: 127.134 kJ/mol; (21)Boiling Point: 834.659 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2c1c(O)c6c(c(O)c1C(=O)c3cccc(OC)c23)C[C@@](O)(C(=O)CO)C[C@@H]6O[C@@H]5O[C@H]([C@@H](O[C@H]4OCCCC4)[C@@H](N)C5)C
(2)Std. InChI: InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21+,22-,31+,32-/m0/s1
(3)Std. InChIKey: KMSKQZKKOZQFFG-YXRRJAAWSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 27800ug/kg (27.8mg/kg)   Journal of Antibiotics. Vol. 32, Pg. 1082, 1979.
mouse LD50 unreported 14mg/kg (14mg/kg)   Biochemical Pharmacology. Vol. 38, Pg. 167, 1989.